


Deal With the Devil

by songofhell



Series: Just Business [2]
Category: Supernatural
Genre: Alternate Universe- No Supernatural, M/M, all other ships are minor, drowley is endgame
Language: English
Status: Completed
Published: 2017-11-16
Updated: 2018-09-23
Packaged: 2019-02-03 04:45:02
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 20
Words: 50,195
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12741258
Author URL: https://archiveofourown.org/users/songofhell/pseuds/songofhell
Summary: The guy was a bastard. He’d made his money off of blackmailing everyone he could dig up dirt on, and now he had roped Dean into being his right-hand. It was disgusting, but… there was just something about the guy.Dean's out of prison, but at a cost. He wishes he could say that he hates working for Crowley, but honestly he's good at what he does, and the company isn't as bad as he pretends it is. But the deeper he gets in with Crowley, the more complicated his relationship with his family becomes. When push comes to shove, Dean will have to make a choice, and it's not nearly as simple as he would have anticipated.





	1. Move-In Day

As Dean pulled up the drive to the black, iron gate that was blocking his way to the large house before him, he was torn between exasperation and reluctant appreciation. Was all this really necessary? But on the other hand… damn, this place looked nice.

He rolled down his window and leaned out to press the buzzer. “Hey, asshat, it’s me,” he spoke into the speaker. “Open up.”

A few seconds later, the gates swung open, allowing Dean to drive on, circling around the small fountain in front of the house to park in front of the expansive front porch. As he got out of the car, the oak front door was opened, and Crowley stepped outside.

Dean blinked at him in surprise; instead of the prison guard uniform that Dean was used to seeing him in, he was wearing an all-black Armani suit with a grey tie. And again… _damn._ He tried not to let his appreciation show on his face as he walked around the car. “Really?” he asked, motioning towards the lavish house. “Was your goal to see how over-the-top you could be?”

Crowley rolled his eyes as he walked down the front steps. “No one’s making you stay, darling.”

“Well, good. Cause I’m only staying as long as I have to. As soon as I have enough for my own place, I’m gone.”

His usual smirk was plastered across his face as he took another step forward, putting himself mere inches from Dean. “We’ll see.” He pulled his hand out of his pocket and held up a key between them. “Your key.”

Dean took it and slipped it onto his keyring. “Also gonna need the code to your fancy-ass gate.”

“6-6-6”

He looked back up from his keys with raised eyebrows. “Seriously?”

“What?” Crowley shrugged. “It’s funny.”

He rolled his eyes. “Sure. That’s what it is.”

“You have no sense of humor,” he sighed.

“I have a great sense of humor!” Dean protested defensively. “It’s not my fault your joke is lame.”

“Others find it funny.”

“Who? The people who work for you because you basically own their souls?”

“And that’s why it’s funny!” Crowley shook his head. “Never mind,” he grumbled. “Where’s your stuff?”

Dean walked around and opened the trunk of the Impala, pulling out two duffle bags.

Crowley’s eyebrows furrowed slightly. “That’s it?”

“Hey, we can’t all be filthy rich,” he snapped.

“Give it time. You will be.” He reached out, taking Dean’s bags from his hands. “Now, how about I take these inside while you park.” He nodded towards the garage connected to the left of the house as he shifted the bags to one hand and fished something out of his pocket. “Here you are,” he said as he handed him a garage door opener.

Dean’s eyes narrowed slightly as he took the item from him without a word and then walked around to get back into his car. He knew full well that Crowley was only being nice to him in an effort to make him more enthusiastic towards the work that they would be doing together. But it wasn’t necessary. Dean didn’t half-ass his work, whether he liked what he was doing, or not. That being said, he saw nothing wrong with letting Crowley think he needed some persuasion. It might make living with the guy more tolerable, at the very least.

It wasn’t that there wasn’t a part of Dean that did – for whatever unfathomable reason – enjoy Crowley’s company, though. Denying that had gone out the window when Crowley had been the only presence that had consistently been able to calm him in prison – had been able to make him feel like the walls weren’t closing in around him. But he knew that every interaction he had had with him, Crowley had been playing some kind of angle. He could see that now, and he had to stop himself from relaxing too much around him – something that he knew would be difficult when his presence made him want to do just that.

What the hell was wrong with him? The guy was a bastard. He’d made his money off of blackmailing everyone he could dig up dirt on, and now he had roped Dean into being his right-hand. It was disgusting, but… there was just something about the guy. He sometimes did or said things that just didn’t fit with the cruel bastard that Dean knew him to be, and… well, maybe now that they were living together he’d get some answers as to who Crowley MacLeod really was. And then maybe he’d stop having this effect on him.

Dean parked the Impala in the garage, next to Crowley’s Bentley – admittedly, a pretty nice car; it had nothing on his Baby, but still – and then walked into the house. The inside was just as nice as he had expected from the outside, and he couldn’t believe that he was going to be living here for the next few months, until he could get on his feet.

A short hall from the garage entrance led to the foyer, but Crowley was nowhere to be found. Dean frowned as he looked around. “Crowley?” he called.

“Up here,” a voice called from upstairs.

He sighed as he followed the voice. He couldn’t wait five fucking seconds for Dean to get inside before he ran off? Seriously?

He found Crowley in the first bedroom on the right. The first thing that he noticed was that the room was too large to be anything other than the master bedroom, and the open closet that contained dark suits and prison guard uniforms only supported that idea. The second thing that he noticed was that his duffle bags were sitting upon the expensive, black comforter of the king-sized bed, and one of them was open. The third thing was that Crowley was currently hanging one of his old, flannel shirts in the closet next to an Amani jacket, and _damn_ did it look as out of place as Dean felt.

He cleared his throat uncomfortably as he shifted his stance in the doorway, rubbing his hand over the back of his neck. “This is your room.”

“Mm,” Crowley acknowledged as he turned to face him with a smirk. “You like?”

Dean cast his eyes once again over the dark walls; the leather couch; the cherry wood headboard; the floor-length, burgundy curtains that covered one wall; the chandelier with small, black lampshades over all the lights… “Yeah. It’s, um… it’s nice. It suits you.”

He arched an eyebrow at him. “Something wrong?”

“I just… didn’t realize we’d be sharing a room.” He had actually never thought much of what their living arrangement would be like beyond wondering how long it would take before they started trying to kill each other. On the one hand, they were already sleeping together, so it made sense that they actually _sleep_ together. But on the other hand… they weren’t a couple, they weren’t even friends with benefits – you had be friends, in the first place, for that label. Really, they didn’t fit into any categorization – they just had sex, and now they were working and living together. And that was dangerous. They didn’t need any more lines blurred between then than there already were.

“Oh.” Crowley’s smug expression fell slightly. “I see. I just assumed…. There are, of course, other rooms. Though they offer far less fun.” He winked.

Dean smirked slightly. “I didn’t realize the fun was contingent on the room.”

“It’s not,” he shrugged. “It does make more sense, though.”

He shook his head slightly, leaning against the door frame. “I dunno, man, doesn’t it seem a little… intimate?” After all, not even he and Benny had slept in the same bed together every night, and they actually _had_ been friends with benefits, in addition to being cell mates.

He chuckled. “That’s your concern?” He sauntered forward, resting his hands on Dean’s hips. “No one but us will know where you sleep, so it’s not as though anyone could use that to jump to conclusions about us, is it? What does it matter what it may _seem_ like, when we know what it is and isn’t?”

 _Did they, though?_ Dean couldn’t help but wonder. Just sex – that was supposed to be all it was. So, why had it felt so damn good whenever Crowley had done everything in his power to get Dean to work for him? Why did feeling so wanted by _him_ mean so much? And why was it that he felt more at ease talking to Crowley these days than he felt talking to his own brother? He didn’t say any of that, though. Crowley didn’t need to know that he might have a greater hold on him than he thought. “I guess,” he muttered instead.

“Really, it’s just practical,” Crowley continued. “I think we both know that you’ll be spending most nights in here, anyway. So, why bother having to go to another room to change all those morning?”

He did make a good point there. But sleeping next to Crowley every night… waking up next to him in the mornings… for some reason that thought was making Dean’s stomach react in a way he didn’t like.

Crowley seemed to sense his hesitancy because he took a step back, tugging at Dean’s hips to encourage him to follow. “Perhaps testing out the bed will convince you. It’s quite soft – and durable.”

An easy smile spread over Dean’s lips as he allowed himself to be pulled towards the bed. Now _this_ he knew how to deal with. Leave it to Crowley to find a way to put him back in his comfort zone. “That so?” he challenged. “Well, then why don’t you convince me that the – _bed_ – is worth it?”

Dean knew that Crowley was strong – to be a prison guard in arguably the worst prison in the country, he had to be – but it was one thing to know, and another to be suddenly dragged around and shoved none too gently onto the bed. He grunted as his back collided with the – admittedly quite soft – mattress, and he stared up at Crowley, eyes wide with arousal. He’d never admit it aloud, but he _really_ liked to be manhandled, and not many of his past partners had been able to do so. Even his previous times with Crowley had been too rushed to allow for much more than a quick, desperate fuck in a storage closet where they had had to be sure to stay as quiet as possible. Now, though, that wasn’t an issue; and Crowley, apparently, wanted to make up for their past by drawing it out for as long as possible.

Dean writhed on the bed, pleading with Crowley as his lips moved over his skin, everywhere but where he desperately needed them.

“I never got the chance to really appreciate your body before,” he said as an excuse, his eyes glinting mischievously. “Which really is quite a tragedy.” He sat up on his knees as he watched his hands’ progress down Dean’s sides. “You are… perfect,” he breathed, his voice so fervent that Dean couldn’t help but blush. He couldn’t remember the last time someone had looked at him like that – like he was something precious.

The gentleness only lasted for a second, though, and then Crowley was making Dean beg, all rational thought flying from the younger man’s mind. If Crowley had already been the best sex that Dean had had, then this was a whole new level – touching on kinks that Dean hadn’t even realized he’d had. Suddenly, moving in with Crowley felt like the best decision of his life.

“So?” Crowley murmured some time later, trailing his lips up Dean’s neck, not at all helping him as he struggled to catch his breath.

“Y-yeah,” he breathed. “Okay.”

He chuckled, allowing his teeth to scrape against skin before pulling away. “Suppose we should get you unpacked, then.”

Dean glowered up at him. “You can’t give me five minutes to recover?”

Crowley smirked. “Oh, sorry. Was I too hard on you?”

He reached up, grabbing one of the pillows beside his head and then throwing it at Crowley. “Shut up.” _You were perfect,_ he added in his head, but he would never say that out loud.

He chuckled again as he returned to pillow to its spot and laid down beside Dean, wrapping an arm around him to pull him closer. “Fine. We can cuddle.”

He rolled his eyes, about to say that cuddling with him was the last thing he wanted, but… it felt nice. Dean’s whole body was exhausted, and as he relaxed against Crowley, his eyes drifted shut against his will. Before he knew it, he had fallen asleep.


	2. Dinner and Dessert

As Dean woke up, he could immediately tell that something was off, but his still partially asleep mind couldn’t quite pinpoint it. Something was missing, though. He rolled onto his back and blinked his eyes open, the black chandelier above him slowly coming into focus. That was it. He hadn’t been alone in the bed when he’d fallen asleep – he’d been playing little spoon to _Crowley_.

He shook his head slightly as though to dislodge the memory from his mind. Cuddling with Crowley was definitely _not_ something that he planned to make a habit of.

He pushed himself up out of bed and pulled his clothes back on, glancing around the room as he did so. His duffel bags that had been pushed off the edge of the bed somewhere along the line were nowhere to be seen. His eyebrows furrowed as he turned and opened the closet door to find the stark contrast of his and Crowley’s wardrobes, his empty duffel bags folded up neatly in the corner.

He rolled his eyes. Apparently, Crowley hadn’t wanted to wait for him to wake up, so he had taken it upon himself to unpack for him. Now he just hoped that he’d be able to find his things. He shook his head as he closed the door, wondering if he had gotten himself stuck living with a control freak.

Speaking of control freaks…. He pulled his phone out of his pocket and pulled up his recent calls, calling the first name on the list.

“Hey,” Sam answered after a couple rings.

“Heya, Sammy,” he greeted him as he sat down on the edge of the bed. “How’s sunny California?”

“Hot,” he chuckled. “Thankfully, the dorm has decent air conditioning.”

“You get all moved in okay?” He’d offered to go down to Stanford to help him move in, but Sam wouldn’t have it – he had insisted that Dean had enough going on with getting his life back together now that he was out of prison. It had almost made Dean cave and tell him that his life was together, but he just couldn’t bear to see the look on his brother’s face when he found out that he was helping to lead an illegal operation. So, he had relented and let Sam go on his own.

“Yeah. What about you?” he asked, concern coloring his tone. “That place you found pan out?”

“Yep. Told you it would. And before you ask – no, the guy is not a serial killer.” Well, at least he didn’t think that Crowley was a serial killer. He wouldn’t put it past him, though.

“So, he seems decent? His ad was honest?”

“Yes,” Dean sighed. “Do you think I would’ve moved in with the guy if not?”

“No, I guess not. It’s just… renting an apartment with a guy you only know from a paragraph he wrote online could go very bad very fast.”

“So you’ve said. Fifty times.” But it wasn’t like he didn’t understand Sam’s concern – he didn’t know that he really had nothing to worry about. “Look, Sam, I’m fine. The guy’s definitely not going to win any congeniality awards, but he’s not half bad. And you know how good a judge of character I am.”

“Yeah, I know,” he sighed. “So, have you started the new job yet?”

“I start tomorrow.”

“Well, I know you’ll do great. No one knows cars better than you do.”

“Dad did,” Dean found himself saying before he could stop himself. A heavy silence fell between them, and he wondered if Sam felt as cold as he suddenly did, even in the California heat. When he was unable to take it anymore, he cleared his throat. “So, you met your roommate yet?”

“Uh, yeah,” Sam muttered, his voice slightly rougher than it had been a few minutes prior. “His name’s Zach – he seems like a nice guy.”

“Good. And if he turns out to be not so nice, just give me a call, and I’ll be down there to teach him a lesson.”

He could practically hear Sam rolling his eyes. “Sure thing, Dean.”

“Well, guess I should let you go flirt with some hot college students.”

“You know that’s not why I came to college, right?”

“What?” he feigned surprise. “Why else would you go?”

“I’ll talk to you later,” Sam ignored the question.

“Yeah. Stay out of trouble.”

“You too.”

Dean hung up the phone with a guilty knot twisting in his stomach. He hadn’t considered how hard it would be constantly lying to Sam and Bobby, but it was already eating at him. He’d just have to get used to it, though – there was no way he could tell them what he was really doing.

He sighed as he rose to his feet and made his way to the door, stopping when he stepped out into the hall. He should probably ask Crowley for a tour of the house sometime soon, so that he wasn’t stuck wandering around like an idiot. There was nothing he could do about that now, though; he was hungry, and he had to find the kitchen somehow. At least he could be fairly certain of the fact that it was downstairs.

As he reached the bottom of the stairs, he scanned the entry way, trying to figure out his best bet. He knew that the hall to his right led to the garage, and it looked like it was a living room behind the French doors to his left. He turned to see what was past the stairs, only to freeze when he found himself being stared down by a very large, black pit bull who did not seem too pleased to see him.

“Woah, um, I’m just gonna…” Dean took a tentative step forward, trying to slip by, but the dog growled, lips curling back to reveal impressive teeth. “Easy…” He held out his hands in a placating gesture. “Heel?” He moved to take another step forward, but the dog let out a sharp bark, stepping closer and making Dean quickly backtrack, before continuing to growl.

“Juliet!” A voice rang out behind him, and immediately the dog’s ears perked up and she let out a bark that was not quite as threatening as the previous one. “Come!”

Dean quickly stepped out of the way as Juliet ran past him to sit in front of Crowley.

“Juliet, this is Dean,” Crowley said, his voice far more friendly than it was whenever he spoke to humans. “He’s going to be staying here. Play nice.”

“You didn’t tell me you had a dog,” Dean grumbled.

He looked up at him with an arched eyebrow. “Is that a problem?”

“It nearly attacked me!”

“She wouldn’t have without cause.”

Dean scoffed. He doubted that. He had never particularly liked dogs, and pit bulls especially he took issue with. It wasn’t necessarily because of their bad reputation, more due to the fact that he had been chased by a pit bull as a kid and it had left a bad taste in his mouth.

“She’s a good girl,” Crowley continued, scratching Juliet behind the ear. “Aren’t you?” he cooed, and she barked. “Yes, you are.”

Dean blinked at the scene before him. _Cute_ was definitely not what it was – he would never think of either Crowley or a pit bull as cute – but it was… definitely something. He shook his head as though that would make the scene change – it didn’t. So, instead he looked away, his eyes coming to rest on a picture of another pit bull on the wall in front of him.

“Don’t tell me you have another dog,” he groaned. Shouldn’t there be some kind of disclaimer about owning dogs before inviting somebody to move in?

Crowley followed Dean’s gaze, his expression falling. “No,” he said sadly. “That’s Growley, he… he was shot. Several years ago.”

Under normal circumstances, he would have made fun of the name, but when he saw the look on Crowley’s face, he couldn’t bring himself to. Crowley hurting over an animal – who would’ve seen that coming? “I’m sorry,” he said instead.

He shrugged, clearly trying to brush it off, even though his expression gave him away. “He got out one day – stumbled across the path of someone who thought all pit bulls are evil. He wouldn’t have…” He trailed off, looking down at Juliet as she licked his hand.

Dean felt a tiny bit of guilt at that. But it wasn’t like he thought all pit bulls were evil, he just didn’t like them. He somehow doubted that Crowley would see much of a difference, though; so, it would probably be best to keep his feelings about Juliet to himself.

“How’d he get out?” he couldn’t help but ask. After all, the entire property was gated, and from the way Crowley clearly was about his dogs, he imagined he took precautions whenever anyone was entering or leaving the property.

Crowley was silent for a couple of seconds. “Can I help you find something?” he asked, as though he hadn’t heard Dean’s question.

“Uh, yeah,” he relented. Clearly, this was something that Crowley didn’t want to talk about, and while that may not always be a deterrent, Dean knew better to press emotional issues. “The kitchen?”

Crowley nodded and walked down the hall, Juliet following at his heels, and Dean fell into step beside him. The pain of loss was still written clearly across his face, and Dean wasn’t sure what to do about it. Some part of him had just assumed that Crowley was incapable of these kinds of emotions, and now that he was faced with the truth, it was hard to be as indifferent to him and he would normally like to be.

“Never would’ve guessed you had a heart,” he said, attempting to lighten the mood.

It worked at least a little – the corners of Crowley’s mouth twitched up slightly. “I’m full of surprises,” he said, sounding more like his usual self.

That he was. And each surprise made even less sense with the person that Dean thought Crowley to be.

“I was planning on ordering dinner soon,” Crowley said as they turned into the kitchen. Juliet stopped at the entrance and laid down. “I don’t cook, so it’s what I usually do.”

“Well, something smells good,” Dean commented, breathing in the scent of whatever was in the oven.

“Yes, I do bake,” he amended, glancing at the clock, and then walking over to put on oven mitts. “It’s actually useful.”

“Uh, cooking’s pretty useful, too,” he pointed out with a laugh.

“Baking is useful for work,” he elaborated as he walked over to the oven and looked inside. “Starting off a negotiation with a baked good is a great way to ensure a more cooperative target – most of the time, at least.”

“Oh, come on. How much can-” He stopped mid-sentence as Crowley pulled the pie from the oven. “Okay, that could actually work.”

Crowley chuckled. “Should I have warmed you up with pie?”

“You might have gotten me sooner,” he admitted, walking closer to examine the pie as it was set down on the counter.

“Well, this had been intended for a certain business owner, but… I suppose it can be your signing bonus.”

Dean smiled. “I might hate you a little less right now.”

He rolled his eyes. “So, getting you out of prison ranks lower than giving you pie. Good to know.”

“Well, it will depend on how good the pie is,” he quickly amended.

“Oh, my pie is the best.”

He raised an eyebrow. “That so? Well, we’ll see about that.”

“I suggest you let it cool first.”

“Well, obviously,” Dean sighed. “In the meantime, what’s your favorite food?”

Crowley’s eyebrows furrowed. “Pardon?”

“I happen to be an awesome cook. And if you’re claiming to make the best pie, I’m gonna show you what I can do.”

He blinked, clearly surprised, then he smiled. “Smoked salmon,” he stated in a voice that implied that Dean couldn’t possibly prepare it to his standards.

Dean didn’t bat an eye. “Don’t suppose you have salmon?”

“As a matter of fact, I do. I keep my kitchen fully stocked, as I’ll sometimes hire chefs to cook for me.”

He rolled his eyes. “Wow. You really are filthy rich.”

“Yes. And I highly doubt that you have anything on the five-star chefs I normally hire to make the dish.”

“Oh, yeah?” he challenged. “Just you wait. And… show me where everything is in here.”

So, a few minutes later, Dean was busy preparing dinner, while Crowley watched with a faintly amused expression on his face. _Hey, at least he’s cheered up,_ Dean found himself thinking.

“I have to admit,” Crowley eventually spoke up. “I didn’t expect you to be the kind of guy who likes to cook.”

“Looks like you’re not the only one full of surprises,” Dean said with a wink, then he shrugged. “I did most of the cooking around the house. Dad wasn’t always… I mean, he could be pretty busy.”

“Yes, John didn’t exactly strike me as father of the year.”

“It’s not his fault we had crappy circumstances,” he immediately jumped to his dad’s defense. “He did the best he could.”

“I never said he didn’t,” he pointed out. “But doing one’s best doesn’t necessarily make for a good father.”

Dean didn’t respond – he didn’t know what he could say. He had always idolized his father, but… he could see now that he had been a long way from perfect. “What did you ask from him?” he asked a few seconds later.

Crowley arched an eyebrow. “I don’t know what you mean.”

“Don’t play dumb,” he snapped. “I know you didn’t give him that information on Azazel for free. What did he do for you?” It was something that Dean had been wondering ever since he’d found out where his dad had gotten his information from, and he couldn’t suppress his curiosity any longer.

“Dean, he was very adamant about the fact that he never wanted you or Sam to find out what he did. I’m not about to go against a dean man’s wishes.”

He nodded thoughtfully. “So, he worked for you?” he guessed.

Crowley didn’t say anything.

“I’ll take that as a yes.”

He sighed. “It was a short-term arrangement.”

Dean’s eyebrows furrowed as he looked up at Crowley. “Why? I didn’t know you did short-term deals.”

“I don’t normally,” he admitted with a slight nod. “But I wanted Azazel gone, so I offered your father a better deal than most.”

He nodded, understanding dawning on him. “And then you saw how good he was and regretted it. So, when you saw a chance to get his son working for you…. That’s why you were so interested in me from the get-go.”

Crowley chuckled. “For someone who can be such a moron, you really are quite smart. You’re mostly right. What you left out is that after I met you, my interest shifted slightly – became less about getting John’s son, and more about getting _you_. There’s just something about you, Dean. I couldn’t explain it if I wanted to.”

Dean rolled his eyes. “I think you just don’t like being told no.”

“Actually, in most cases, I’ll relent – maybe make the person’s life miserable, but I’ll stop trying to recruit them. I couldn’t do that with you, though. And I’m glad I didn’t. I can already tell that you’re going to prove to be even an even better recruit than your father.”

He shook his head, remembering all the years he had looked up to his dad, hoping to one day be as good at everything as he was – and then when he had realized that he would never be as good, but he was determined to get as close as he could. “I doubt that.”

“I don’t,” Crowley said confidently, fixing Dean with a level gaze. “Not even a little.” There was such conviction in his eyes that Dean found himself blushing slightly as he turned back to the food he was preparing.

Once dinner was ready, Crowley led the way to the dining room, and they sat down at the table, Crowley with a dish of smoked salmon pasta in front of him, and Dean with a slice of apple pie in front of him, his own pasta pushed off to the side for the time being.

“Ready?” Dean asked, his fork hovering over his pie.

Crowley ensured that he had a good proportion of salmon and pasta on his fork before turning to him. “Ready.”

They both took a bite.

“Oh my god,” Dean groaned around the pie in his mouth, his eyes slipping shut as he savored the taste. As much as he hated to admit that Crowley was right about how great his pie was, it was hard to be bitter when he was eating said pie.

As he swallowed his bite, he looked over at Crowley, who was chewing with a thoughtful expression on his face. “So?” he questioned, more nervous to hear the verdict than he had expected to be. He couldn’t explain why, but he really wanted Crowley to like his cooking.

His expression was unreadable as he swallowed and turned back to Dean. “It’s not how I normally eat salmon,” he began, and Dean felt his heart drop. “That being said… it is quite delicious.”

He perked up. “Yeah?”

He nodded. “I’ve actually only had smoked salmon pasta once before, and I hated it. So, I think it’s safe to say, this is the best I’ve had.”

Dean beamed. “Didn’t I tell you?”

“You did. I suppose I should’ve learned by now to give you more credit. So.” He gestured to the slice of pie. “Do you admit it’s the best pie you’ve had?”

His smile slipped slightly – enjoying the pie and giving Crowley the satisfaction of knowing he was right were two different things. “The best _apple_ pie. I couldn’t possibly compare it to others.”

Crowley chuckled. “Suppose I’ll have to make you more kinds of pie, then.”

“No complaining here.” He took another bite of the pie. If living with Crowley involved getting to show off his cooking skills and eating as much pie as he wanted, maybe this living arrangement wouldn’t turn out to be so bad, after all.


	3. Introductions

Living with Crowley was certainly an adjustment. The sex was great, of course, but it was a little awkward rolling to opposite sides of the bed to fall asleep afterwards. Dean wasn’t used to sleeping in the same bed as somebody without cuddling – not that he wanted to cuddle with Crowley, because he _didn’t,_ it just took some getting used to. Then there was the time that Crowley had accidently woken him up when he had gotten up for work, and his half-asleep self had thrown a pillow at him and yelled at him to be quiet. On top of all that, he was also forced to deal with Juliet on his own whenever Crowley was at work, and he swore the dog hated him.

“It’s because you’re rude to her,” Crowley said when Dean brought this up.

“I’m not rude to her!” he protested.

“You never show her any affection – you never even look at her, if you can help it. Of course she doesn’t like you!”

The worst part was the boundaries, though. It wasn’t so bad in the mornings, as Crowley was generally gone by the time Dean got up – either at work at the prison or running errands for his (well, now _their)_ side business – but the rest of the time, the combination of living and sleeping together was causing lines to blur between the two of them. After Crowley had taken a pillow to the face that one morning, he’d merely chuckled, then kissed him and told him to go back to sleep – Dean might’ve thought it’d been a dream, if it weren’t for the fact that he’d never dream _that._ Then there was the day that Crowley had gotten home while Dean was cooking dinner – he’d come up behind him and placed his hands on his hips as he took a peek at what he was making, and for some unbeknownst reason, Dean had leaned back into him and kissed him. Of course, kissing Crowley was fine, but these kisses were all wrong – they were soft and tender and implied something that was definitely _not_ true.

But _this_ morning…. It was Crowley’s day off at the prison, and nothing was going on with their little blackmail ring until later in the day, so he was sleeping in. Dean was aware of this, and he hadn’t thought anything of it, until he woke up curled into Crowley’s side, with his head resting on his chest.

How the hell had this happened? He replayed the previous night in his head (which might not have been the best idea, considering that he was pressed up against Crowley) – they had had sex, then turned away from each other, just like always. So, how had they ended up like this? Had this happened before? How many times had Crowley woken up to find Dean clinging to him like this?

He took a deep breath. He was probably making too big of a deal out of it. It was probably just a fluke thing – they had moved in their sleep and had somehow ended up like this. It wasn’t that weird… right? He just needed to figure out how to move away without waking up Crowley.

He shifted slightly, pulling his arm back from around Crowley’s waist, when a voice from above his head made him freeze.

“Morning, darling.”

 _Dammit._ “Morning,” he replied as casually as possible. Crowley didn’t need to know how embarrassing this was for him, or else he’d never hear the end of it.

Crowley shifted slightly, his leg rubbing against Dean’s half-hard cock and causing him to draw in a sharp breath. “Sleep well?” he asked as though he hadn’t noticed anything – not that Dean believed that for a second. Hell, Crowley had probably moved like that on purpose.

“Not really,” he lied. “I kept half-waking up, uncomfortable, then falling back asleep before I could figure out what the problem was. Guess I figured it out.”

“Hmm,” he hummed thoughtfully, shifting again. “You seem plenty comfortable to me.”

“Morning wood doesn’t mean I’m comfortable, jackass.”

“Then how do you explain the fact that you didn’t get hard until you woke up?”

Dean didn’t say anything, gritting his teeth together as he glared at the bedroom door. He really hated it when Crowley was right – especially when he was right about him, and that happened more often than he cared to admit.

“Oh, stop pouting,” Crowley said exasperatedly. “We don’t have to start getting things ready until noon – that leaves plenty of time to take care of your little problem.”

He rolled his eyes as he pushed away from him. “I’m good, thanks,” he muttered as he got out of bed. It was bad enough that Crowley was right, the guy didn’t need that satisfaction of getting laid, too.

Crowley raised his eyebrows as he sat up. “Are you _really_ being this petty?”

“It’s not being petty. Contrary to what you seem to think, I _do_ actually have better things to do than having sex with you.”

“Oh? Like?”

“Like making sure I don’t make a fool out of myself at this meeting tonight. Come on, I want to make sure I know everything I need to know.”

Alright, so maybe going over the ins and outs of Crowley’s business for the third time this week wasn’t Dean’s first choice of how to spend the morning, but it was better than giving into Crowley. Besides, this was his first time meeting the others involved in the organization, so it was for the best that Dean make sure he knew everything he needed to know. As Crowley had informed him earlier in the week, the majority of the team wasn’t too thrilled about the newest addition.

“Here’s my credit card,” Crowley had said, handing Dean the platinum card. “While I’m at work today, go buy yourself a nice suit.”

“Why?” Dean had frowned down at the card as he’d taken it from Crowley’s hand.

“You need to present yourself well when we meet with the others on Friday.”

“I didn’t realize your little organization had a dress code.”

“It doesn’t,” Crowley had sighed as he usually did whenever he felt that Dean was being particularly thick. “But it would be in your best interests to present yourself well – and wearing one of your ratty flannels won’t do you any favors.”

“You know, I really don’t care what a bunch of criminals think of me.”

“You should care that they respect you. Which they won’t. A good portion of them have been fighting to be where you are for years, and now here you come, brand new and immediately at my right hand. You should’ve seen their faces when I gave them the news. They all hate you – you should do what you can to lessen that.”

So, after everything was prepared that Friday, Dean dawned the stuffy (in his opinion) suit he had bought and joined Crowley in the foyer. Judging from the look on his face, though; he didn’t think the suit was stuffy at all.

“You should wear a suit more often,” he murmured in a low voice, smoothing the front of Dean’s jacket for no good reason other than to touch him. “I’m going to quite enjoy tearing it off of you tonight.”

Dean licked his lips, suddenly thinking that maybe the suit wasn’t so bad, after all. “Can’t wait.”

Unfortunately, not only did he have to wait, but he also had to maintain professional composure as their business partners began to arrive.

The first arrival was a well-dressed woman with straight, brunette hair and sharp features. She walked through the door as though she owned the place, and her expression as her eyes landed on Dean was both calculating and full of resentment. Well, this was off to a great start.

“Mrs. Burrows,” Crowley greeted her cordially. “I hope you are doing well.”

“Just fine,” she replied a bit stiffly.

“This is Dean Winchester.” He waved a hand towards Dean with a small smile. “The man I told you about. Dean, this is Marsha Burrows.”

“I’ve been working for Crowley for ten years,” she boasted as she held out her hand for Dean to shake, although the look in her eyes clearly said that she would much rather be raking her long, manicured nails across his face. “I have brought in numerous, invaluable connections to the operation – there is no way that it would be as successful as it is without me.”

“Yeah…” Dean muttered as he stepped forward and shook her hand, meeting her eyes with a steady gaze. “Pretty sure Crowley’s successfulness is not all that dependent on you.”

Marsha looked aghast as she dropped Dean’s hand, her gaze snapping to Crowley, who was regarding them both with raised eyebrows and an amused expression. “What, did you not even train your new lap dog to behave civilly? He could ruin our business!”

“I think he’ll do just fine,” Crowley said smoothly, his gaze lingering on Dean before moving to Marsha. “I would only put the very best in his position.”

She huffed. “I’ll just wait in the dining room, shall I?” She didn’t wait for a response before she strode off in that direction.

Once she was gone, Crowley leaned in close to Dean. “What happened to trying to make them like you?” he asked in a low voice.

Dean shrugged. “She was never gonna like me. Might as well make a point – I’m not about to back down just because I get some hostility.”

He was silent for a second, and Dean thought he was about to be rebuked, but then he said, “Have I mentioned how glad I am I hired you?”

He looked at him in surprise. “No. But if you want to, by all means, go ahead,” he added with a grin.

Crowley chuckled. “Well, Dean, I am _exceptionally_ glad to have you at my right hand. I think we will go far together.”

Dean found himself smiling at Crowley’s words. “Yeah, I think we will,” he agreed honestly. As much as he may not want to like this work, he knew he was good at it, and he would be hard pressed not to enjoy the pride of a job well done.

Crowley opened his mouth to say something, but at that moment, the door opened and a woman in a blue dress, with wavy, light brown hair and a predatory smile entered the house.

“So, you must be Dean Winchester,” she spoke up before Crowley could say anything. “The man who rose to the top, straight from prison.” She walked forward, moving in a way that definitely caught Dean’s attention, and held out her hand. “Congratulations.”

“Thanks,” Dean said, shaking her hand cautiously. Even though her words seemed friendly enough, Dean could tell that she was a lot more dangerous – and potentially hostile – than she let on.

“Dean, meet Bela Talbot,” Crowley supplied. “One of the best and brightest.”

Bela smirked as she dropped her hand to her side, her eyes still fixed on Dean. “I have to say, Crowley, I can see what you see in him.”

“I’m sure you can,” he said curtly, some of the warmth leaving his voice. “Mrs. Burrows is waiting in the dining room. Perhaps you would like to join her?”

Her gaze shifted to Crowley, and she nodded. “See you boys soon,” she said as she walked away.

Dean watched her go until the door opened again, and he turned to meet Carl Granville.

As more people arrived, Dean decided that Marsha was definitely who had wanted to be at Crowley’s right hand the most, but that wasn’t to say that others didn’t look ready to fight him for the position, as well. Most were at least civil to Dean, while glaring daggers at him, but some were apparently too put out to even pretend.

“Oh, now I get it,” Lester Morris said when he saw Dean. “You slept with him to get the job, right?”

Dean’s eyebrows shot up, and for the first time since people had started arriving, he didn’t know what to say. Because, well, he _was_ sleeping with Crowley, but that wasn’t how he had gotten the job. At least… he didn’t _think_ that was how.

“Come now, Lester,” Crowley interjected. “You know I have a strict policy about not sleeping with employees.”

Dean waited until Lester left the room to turn to Crowley with an eyebrow raised in question.

He sighed. “In my defense, you weren’t my employee when we started sleeping together.”

“Yeah, but I am now.”

“Yes; however, I do not feel enough conviction towards the policy to stop something I quite enjoy.”

Dean laughed. “Fair enough.” He certainly wasn’t complaining. “This has to be about everyone, right?” he asked, glancing back towards the door.

“There’s one left.” Crowley looked at his watch. “Late, as usual.”

“Who-?”

“Ah, I think I hear his car,” he interrupted, moving to look out the window.

A few seconds later, the door opened and Dean’s jaw dropped. “Holy _shit,”_ he breathed.

“Dean, this is-” Crowley started, but Dean cut him off.

“Gunner Lawless.” He walked forward, holding out a slightly shaking hand with a star-struck smile on his face. “I’m a big fan. I – I got to tell you, I... worshipped you, growing up.”

Gunner smiled as she shook Dean’s hand, his eyes flickering briefly over towards Crowley, who was frowning slightly. “Thanks. So, you must be the newbie – Dean, right?”

“Yeah.” His smile somehow managed to grow at the fact that _Gunner Lawless knew his name!_ “Yeah, that’s me. I – I didn’t know I’d be working with you, though. This is awesome.”

He glanced down to where Dean still held his hand in a tight grip. “I plan on keeping that hand.”

“Oh, sorry.” He dropped his hand. He opened his mouth again, intending to recall his favorite match that his dad had taken him to as a kid, but Crowley stepped up to them.

“Everyone else has already arrived. If you be so kind as to go find yourself a seat, to prevent us from starting any later than you have already put us.”

Gunner rolled his eyes. “Sure thing.”

Dean watched him go, his awestruck expression still in place, then turned to Crowley, who was closing the gates to the property. “Dude, you didn’t tell me that _Gunner freakin’ Lawless_ works for you!”

“Yes, he does,” Crowley sighed, his expression irritated as he turned back to Dean. “Do try to act professional.”

He frowned. Was it just him, or had Crowley’s mood just abruptly soured? “What’s your problem?”

“My problem is that you’re making a fool out of yourself in front of a subordinate,” he snapped. “Now, come on. We’re starting late enough as it is. Just try not to drool over Lawless the whole meeting.”

Dean rolled his eyes as he followed Crowley to the dining room. He wasn’t _drooling_ (he brought his hand up to his mouth just to be sure – nope, definitely no drool). He didn’t know what Crowley was going on about.

 


	4. Jealousy

“Look, we have the dirt on her,” Marsha insisted. “Let me arrange a meeting with her, and I’ll have her under our thumb in no time.”

“No,” Crowley objected immediately, his voice firm. “We don’t have enough. Abaddon won’t cave so easily.”

“How do you know? We have to be willing to take risks! That’s the only way-”

“We take _calculated_ risks, and we profit,” he interrupted harshly. “If we go in with enough to do no more than anger her, we lose our shot.”

“I’ll take it one of your pies wouldn’t be enough to tip the scales in our favor?” Dean checked, earning a snort from Marsha.

“Unfortunately, I don’t think so,” Crowley said, but Dean was glad to see that at least he wasn’t acting like the question had been completely ridiculous.

“You could try the muffins again,” Lester suggested.

“Because that worked so well with Roman,” Gunner chuckled.

Dean’s brain, which had been occupied with trying to come up with a feasible strategy, came screeching to a halt. “Roman?”

There was a faint smirk on Crowley’s face as he turned to face him. “I offered a deal to Dick Roman when he was on the rise. He refused. Then he proceeded to make things as difficult for us as he possibly could – until _someone_ was courteous enough do away with him for good.”

Dean’s eyebrows shot up. “You tried to make a deal with Dick Roman? Were you ever gonna tell me about that?”

“Why does it mean so much to you?” Bella asked curiously.

Crowley’s smirk broadened as he turned back to the others. “Well, for starters, Dean here is who killed Roman.”

That certainly got some raised eyebrows and shocked expressions.

Gunner blinked, then whistled as he leaned back in his chair, his eyes running over Dean thoughtfully. “Guess you’re more than meets the eye, huh?”

“That does beg a rather intriguing question,” Bella spoke up before Dean could reply, leaning over the table with an almost predatory smile. “How did you managed to get out of prison after that – assuming you didn’t escape, that is.”

Dean glanced at Crowley out of the corner of his eye to see him shake his head just slightly. “I was acting in defense,” he answered. “Evidence was finally found to prove that.”

“Lucky you.”

“And lucky _us_ that I was able to snatch him up,” Crowley added. “Now, back to business. We need more dirt on Abaddon. Any suggestions?”

Everyone was silent for a minute as they thought. Dean was fully aware that the little respect he had earned with the revelation that he had killed Dick Roman would vanish soon enough if he couldn’t prove himself in the position he now held. And now, while he had already broken through to them slightly, was his best chance to do that.

“I’m assuming you’ve already spoken to past associates of hers?” he asked.

“Marsha?” Crowley turned to her with an eyebrow raised in question.

“Of course,” she answered immediately. “I tracked down everyone from the past five years. None were willing to speak against her.”

“Just the last five years?” Dean asked.

“Well, yes. I hardly saw the need to go back further. That was before she moved to the area.”

“That doesn’t mean some dirty little secrets from before she moved couldn’t be useful, though.”

Marsha bristled. “The odds of finding something out from that far back-“

“I’ll take care of it, then, if you’re not up to it.”

Crowley chuckled softly beside him, while Marsha’s jaw dropped. “I can-” she stammered, but Crowley cut her off.

“Not a bad idea. Dean, you have a week to dig up something new. If you cannot, Marsha can try again.”

“Sounds fair enough,” Dean agreed, hoping that a week would be enough time. Honestly, he didn’t feel like it would be, but he knew that Crowley wanted him to prove himself, so surely he’d be giving him a reasonable deadline.

“You really think his first assignment should be _Abaddon?”_ Marsha demanded. “Shouldn’t he start a little smaller scale?”

“I am confident that he can handle it,” Crowley assured her. “But if anyone else has any objections…”

“I kinda want to see what he can do,” Gunner said with a grin.

“This isn’t the time for experiments,” Marsha protested hotly.

“He’s just talking to people from Abaddon’s past – how badly can he screw that up?”

“I believe that it would be in the best interest of our operation to not find out.”

“Well, I think we should give Dean a chance,” Bella voiced. “See if he’s more than a pretty face,” she added with a wink. “If he’s not, we’ve done worse damage control.”

There were a couple murmurs of agreement, and Crowley clapped his hands together. “That settles it, then. Dean, you have a week.”

“Not a problem,” Dean said, more confidently than he felt.

After that was decided, the meeting was wrapped up with a few formalities, and then everyone was invited to stick around for drinks. Marsha, of course, left at the first opportunity, and a few followed after her, albeit with at least a somewhat greater attempt to be polite as they took their leave.

Dean was pouring himself a glass of Crowley’s outrageously expensive Scotch (one of his favorite things about living with him), when he felt a gentle hand on his arm. He turned around to see Bella standing there with a flirtatious smile. “Oh. Hey, Bella.”

“Hello, Dean.” Her hand slid down his arm slightly, though she didn’t remove it. “You know, I have to admit, my expectations weren’t high when Crowley told us about you, but now that I’ve met you, I think I may have been a little harsh in my judgment.”

“Well, I… appreciate that,” he said with an air of caution.

“That being said, if you need _any_ help with your assignment – some may see it as a weakness, but I think it’s a strength to be able to turn to someone else when in need. So, if you come to me, I promise that it will stay between us.”

Dean smiled, but he still got the sense from her that she wasn’t being entirely honest. “Thanks, but… I think I’ll be good.”

“Of course.” Her smile didn’t waver as she took a step forward, bringing them mere inches apart. “Maybe we can just do dinner, then?”

A hand came down on Bella’s shoulder. “I think Dean would like some space to breath,” Crowley nearly hissed, an undercurrent of anger in his voice.

Dean blinked at him in surprise, an almost… warm feeling welling inside him.

Bella turned her head to arch an eyebrow at him. “I don’t hear him objecting.”

“Only because he’s too nice to outright tell you he’s not interested. I suggest you back off.”

“Is that so?” she challenged.

“Yes, it is,” he said coolly. “I know what you’re trying to do, and it is one of the reasons you will _never_ be at my right hand. Now, I suggest you go.”

They stared each other down for another couple of seconds. Dean had no idea of the expression on Bella’s face, finding that he was unable to tear his gaze away from the intensity of Crowley’s glare. Eventually, she dropped her hand from Dean, then spun on her heel and stalked away.

Dean assumed that she was leaving the house, but he didn’t turn away from Crowley to look. “What the hell was that about?” he demanded in faint disbelief.

He blinked at Dean, the anger in his expression dissolving into a rather convincing display of innocence. “What was what about?”

He rolled his eyes. “Oh, come on. You being all possessive. We never said anything about being exclusive.” And he didn’t _want_ to be exclusive with Cowley… did he? Of course he didn’t, why did he even have to ask himself that? And why was his heart rate accelerating as he waited for a response?

“No, we didn’t,” Crowley answered quickly, his tone hard to read as his gaze settled just to the left of Dean. “We’re not.”

“Alright…” Dean scrutinized him, trying to figure out what was going on. There was something about the set of his shoulders, the look in his eyes… it couldn’t be…. “Are you… are you _jealous?”_ he asked with a half-laugh.

His jaw clenched as his eyes snapped back to him. “Don’t be ridiculous. I don’t get _jealous._ Bella was only interested in screwing you over so that she could get your job. You should be thanking me.”

“Well, sorry to break it to you, but you ain’t some knight in shining armor. I figured it was something like that, and I wasn’t about to trust her. And I would’ve handled the matter a lot more delicately than lashing out in a jealous rage.”

“I am _not_ jealous!” Anger and desperation painted his face, at odds with his words.

“Right. It was just about Bella. So…” His eyes scanned the crowd until they landed on his target, and he jerked his chin in his direction. “If I was to ask out Gunner over there…”

Crowley snorted with laughter. “Your celebrity crush? By all means, go ahead. I could use a good laugh.”

Dean smirked as he walked forward, knocking against Crowley’s shoulder as he passed him. Some part of him wondered if Crowley was going to try and stop him. Another part wondered if he wanted him to.

“Just don’t come crying to me when he turns you down,” was all he said, though.

As Dean approached Gunner, the confidence he had possessed while talking to Crowley vanished to be replaced by nerves. “Gunner,” he somehow managed to say without his voice shaking.

The wrestler turned to him with a smile. “Dean. What’d you think of your first meeting?”

“Oh, you know – everyone seems super nice.”

He chuckled. “I’m sure they’ll all start pretending more once they realize you’re not going anywhere.”

Dean’s smile slipped slightly. “That what you’re doing?”

“Nah.” He shook his head. “Never had much interest in rising in the ranks. Not like some. Speaking of which, I saw Bella trying to work her magic on you. She strike out?”

He had noticed that? Did he care if Bella had caught his attention? He felt a surge of hope. “Yeah, I have my eyes set elsewhere,” he said with a smirk.

Gunner raised his eyebrows slightly. “Really? You don’t think I’m a little old for you?”

He shrugged. “Is it weird that I kinda like older men?” _Like Crowley,_ some intrusive part of his mind whispered. _Shut up!_ the more conscious part of his brain shouted back.

“Well, I certainly don’t mind,” he said smoothly.

“Well, good.” His grin was a mix of excited and nervous. “So, you doing anything tonight?”

“How about you?” he suggested cheekily.

Dean’s breath caught in his chest, and he had to clear his throat before he could speak. “No objections here,” he said slightly breathlessly, knowing that his cheeks were probably red.

“Want to start with dinner?” he asked with an amused smile. “Let’s say, seven at The Glasshouse?”

Dean knew The Glasshouse only by its reputation of being one of the nicest five-star restaurants in the area. “You sure we’ll be able to get a table?”

He nodded. “Working for Crowley has its perks – one of which is connections in high places, such as the owner of The Glasshouse. I’ll get us a table.”

“Sounds great, then.”

“Guess I better get going, then, if I have a date to get ready for.” He winked at Dean then made his way to the door.

As Dean turned away from him, his gaze rested on Crowley, still standing back where he had left him, his expression a mix between livid and… something else. And while that should have been satisfying for Dean – his expression did basically achieve his goal of proving that he was, in fact, jealous – there was just something in his eyes that made him feel guilty, instead. He shook those thoughts from his head as he turned away. It didn’t matter how Crowley felt. He had a date with Gunner Lawless tonight, nothing could get him down.


	5. Date Night

Dean definitely wasn’t freaking out over what he was going to wear on his date. Nope. Definitely not. He just… thought he should try just one more shirt.

“You’re pathetic,” Crowley’s voice came from the doorway as Dean held the up the shirt he had just plucked from the closet, comparing it to the one he was currently wearing.

He looked over at him irritably. “Just because you’re jealous, doesn’t mean you have to insult me.”

“You’re still on that?” His expression was cold as he stepped further into the room, his eyes locked on Dean’s. “I assure you, Dean. Even if I were the jealous type, I would not be jealous over _you.”_

Dean rolled his eyes, telling himself that he didn’t believe that for a second as he ignored the slight sting of the words. “Then why so pissy?”

“Because I’m tired of your insolence,” he shot back. “Going on a date with an employee just to piss me off is in poor taste, even for you.”

“Well, never fear – I’m going on the date because I want to. It has nothing to do with you.”

“You asked him out immediately after accusing me of being jealous,” he pointed out exasperatedly.

“I can do something I honestly want to prove a point, you know.”

He perked up slightly. “So, you admit you did it to prove a point.”

“What does it matter?” Dean demanded. “I got a hot date _and_ proved that you’re jealous – win-win.”

Crowley chuckled humorlessly as he took another step forward. “Oh, darling. In order to be jealous, I would have to care about you. Which I don’t.”

He tried to laugh at that, despite the uncomfortable way his stomach seemed to be tying itself into a knot. “Right. That’s why you tried so hard to get me, took care of me in prison, invited me to move in with you…”

“You thought that meant I cared?” he asked with raised eyebrows. “I don’t _care,_ Dean. About anyone. And especially not you. It was just business. You are a valuable asset – I needed you on my team, and I did what I had to do to get that. You are a business move. Nothing more.”

Dean felt as though he had been plunged into ice water, but he was still fighting to keep his head above the surface. “And sleeping with me was… what?”

“I never said I wasn’t attracted to you. That’s entirely different.”

“Right….” The water was starting to fill up his lungs. He was finding it difficult to breath. “Well, it’s not like I care,” he employed his best defense, his voice surprisingly level, despite feeling like he was drowning. “Now, could you get out so I can get ready for my date? I’m looking forward to spending time with someone who’s actually a decent human-being.”

He thought for a split second that he saw something flicker in Crowley’s eyes, but before he could pinpoint it, he was turning away and walking for the door. “Don’t even think about bringing him back here tonight,” he paused at the door to say.

“Of course not.”

As Crowley shut the door behind him, Dean sank onto the bed, the nerves that had been consuming him just minutes before now replaced with an ache that he didn’t want to look too closely at. Why the hell did this hurt so damn much? It wasn’t like Crowley’s feelings for him mattered at all – Dean hardly even liked the guy, he certainly wasn’t looking to settle down with him. But like an idiot, he had let himself get caught up in the way Crowley was treating him, and he had forgotten the kind of person he really was – the kind of person who didn’t care about anyone but himself and would use people up in a heartbeat to get what he wanted. And somewhere along the line, Dean had deluded himself into thinking that he actually meant something to him, that he was more than just a pawn in his game.

He thought it all through until he was satisfied that the ache in his chest didn’t come from his own feelings, rather than from his expectations being shattered yet again. Which was a perfectly rational explanation.

He shook his head as he got back to his feet, trying to drive all thoughts of Crowley from his mind. He had a date with a guy who had occupied a great many of his fantasies growing up, so there was no time to mope over some asshole that he hated. There also was no longer time to change his shirt, so he grabbed his wallet and keys from the dresser and made his way to his car, mercifully not running into Crowley along the way.

When he arrived at the restaurant – about fifteen minutes late – Gunner was waiting outside the building.

“Sorry I’m late,” he said as he walked up. “Crowley decided to give me a lecture on dating employees.” It wasn’t _that_ far from the truth, and the more he could blame on Crowley, the better, in his opinion.

“I’ll take it you decided not to listen?” Gunner asked as he walked through the first set of double-doors to the restaurant, Dean following behind him.

“Told him he could shove his rules up his ass,” he confirmed. While he may not have done so in so many words, he certainly would if the opportunity should present itself.

He glanced back at him with raised eyebrows. “You are brazen.”

Dean shrugged. “I see no reason to play nice when I hate someone.”

A surprised expression flitted across Gunner’s face, but as he had been in the midst of opening the second door, he didn’t have a chance to say anything before the host greeted them. “Hello. Do you have a reservation?”

“Lawless.”

He glanced briefly down at his book before smiling up at them. “Right this way, sir.”

After they were seated and got their drinks ordered, Dean glanced up from his menu to see Gunner looking at him with a curious expression. “What?” he asked, a bit self-conscious.

“You’re Crowley’s right hand,” he said slowly.

“Yeah. And?”

“And you hate him. That doesn’t add up.”

“It’s not like I volunteered for this,” he said with a humorless laugh. “He manipulated me into joining him, just like he did with everyone else.”

Gunnar’s lips quirked up in an amused smile. “You seem awfully confident in that for someone who just joined up.”

“Yeah?” Dean challenged. “How did he get you to join up, then?”

“My career had taken a turn for the worse,” he explained. “Crowley had the connections to get me back in the ring.”

“See?” He motioned at the space between them triumphantly. “Manipulation.”

He chuckled. “You could call it that, I suppose.” He shifted his attention back to his menu, letting the conversation drop.

Dean didn’t want to drop the conversation, though. He wanted Gunner to agree with him that Crowley was one of the worst people on the face of the Earth, he wanted to see how miserable the people working for him were just to reinforce that fact. He also wanted the date to go well, though; so, instead he turned back to his menu, trying (and failing) to push thoughts of Crowley from his mind.

After they ordered their food, the conversation started flowing a lot easier than Dean had figured it would. He and Gunner were actually a lot alike, and that realization made it easier for Dean to loosen up and talk to him with freaking out quite as much over being on a date with his celebrity crush. Gunner asked him about his time in prison, and Dean told him just how awful it had been, which then led to them talking about all the times they had been roughed up and comparing scars.

“I've been beat up, spit on, stabbed, roughed up,” Gunner was saying with a passion that Dean had already noticed was only in his voice when he was talking about wrestling. “But I will be damned if I didn't always get back up. One thing I learned, you got to keep on grinding no matter what's thrown your way.”

“Damn, you’re awesome,” Dean couldn’t help but say, a slightly awed smile spreading across his face. But then he realized something, and his smile slipped slightly. “So, that’s why you took the deal with Crowley, huh?”

He nodded. “Damn right. I wasn’t giving up that easily.”

“Was it worth it, though? I mean, I’m all for not giving up, but working for Crowley, being at his beck and call till he says, ‘that’s enough’ – which probably won’t happen till he’s dead – isn’t exactly what I call a good way to live.”

“Sure, it’s not ideal,” Gunner acknowledged. “But some extra money and great connections… the price could be worse. I’m not being asked to kill anyone.”

“Yet.” Dean motioned with his forkful of steak. “I could see Crowley doing something like that, though.”

He raised his eyebrows. “Seriously? I know Crowley may not be the most upstanding person in the world, but he does have some morals.”

Dean scoffed. “The guy’s a heartless bastard who doesn’t care who he steps on to get what he wants. He’s a freakin’ psychopath!”

“A psychopath?” he asked slowly. “Dean, I think you may be-”

“Okay, when I was in prison, he blackmailed me using his supposed ‘friend’s’ little brother. If he had any compassion for his Gabriel, there’s no way he would have threatened Cas like that.”

“Sometimes business gets in the way of friendships. It’s unfortunate, but I’ve had to make choices like that, too.”

“With Crowley it’s different, though,” he argued fervently. He felt compelled to make sure that Gunner – and just about everybody else, for that matter – knew just how much of a bastard Crowley really was. “When I say he manipulated me…” He paused. He couldn’t go into too much detail; Crowley had made it clear enough that people couldn’t know that they had been sleeping together. Of course, that kind of made him want to tell Gunner even more, but he probably had a good reason for wanting that to remain quiet, so Dean quickly edited the story. “When I was in prison, he did everything he could not just to keep me safe, but to try to make things better for me. Even after I got out of our original arrangement, he kept acting like he actually gave a shit about my wellbeing. Turns out he was just buying time to get more leverage. And that’s all it ever is with him. I mean, just a little while ago he straight up told me he doesn’t give a shit about anybody.”

Gunner was quiet for a moment, his eyebrows furrowed as though he was deep in thought. “I’d say the same thing if the guy I liked was about to go out on a date with someone else,” he finally said, his tone hard to read.

The anger that had been coursing inside Dean abruptly cooled as though doused with water. “W-What?”

He chuckled softly. “I saw the way he watched you today – he clearly cares something for you, I just didn’t realize how much until just now. Crowley is the type of guy who would never tell someone that he likes them because he doesn’t want to be seen to have any soft spots. He has them, though. You seen him with his dog?”

He did have a point there. Dean didn’t say anything, though; he was looking down at his plate, trying to wrap his head around what he was being told.

“And if that someone were to hurt him – say, by going out with someone else – his first instinct would be to hurt them right back – perhaps by proclaiming that he doesn’t give a shit about them. I’d bet everything I’ve ever won that if you open your eyes, you’ll see that what he said doesn’t quite add up with the things he’s said and done in the past.”

That was easier said than done. He didn’t want to look back at all the discrepancies between the way Crowley had acted towards him and the kind of person he labeled him as. It was so much easier to be angry and hate him than to think… _could_ he actually like him like that? The way Crowley had acted towards him since they had moved in together had been rather… couply. And even before that, he had been so protective of him in prison, had really seemed to care, going beyond what he had to do to recruit him….

The realization must have been clear on Dean’s face because Gunner nodded. “Now, while I really wouldn’t mind dating someone the boss has his eyes set on… I’m not to fond of dating people whose attention is elsewhere. And frankly, I get enough of Crowley at work, I don’t need to hear about him quite this much. So, maybe you should ask him out instead.”

Wait, Gunner thought that _he_ liked _Crowley?_ That was… less ridiculous than it should be. He remembered back when he and Crowley had just started sleeping together, and Dean had felt at ease around him in a way he had never thought he would feel in prison. He remembered the hurt and betrayal he had felt when he had thought that Crowley had just been sleeping with him to buy time, and then the way Crowley had refuted that and said that he’d give him everything he wanted because ‘he deserved it.’ He remembered the joy he had felt at something as simple as Crowley liking his cooking. He remembered just earlier that day, waiting in the foyer, how at ease he had felt flirting and laughing with him. And then he remembered how it had felt when Crowley had said he didn’t care about him. Oh. Dean swallowed thickly. What the hell was he supposed to do now?

As he looked back up at Gunner, a kind of calm came over him. If Crowley’s feelings for him got out, it could be very bad for him. So, he directed his focus towards protecting the man he apparently had some really complicated feelings for, the rest he could deal with later. “You can’t tell anyone.”

“I won’t,” Gunner vowed, his tone sincere. “You have my word on that. I’ve never been once for causing drama. And I respect Crowley – the fact that he has human feelings doesn’t change that.”

Dean nodded. “Thank you.” He glanced down at his plate, then back up at Gunner. “You want to… finish dinner?”

“Sure,” he agreed with a grin.

The rest of dinner passed with a surprisingly little amount of awkwardness, all things considered. They continued to talk and laugh, then they said their goodbyes, and Dean opted to go on a walk to clear his head before returning home.

He liked Crowley. As much as he would love to deny that, he really couldn’t anymore. Not when Gunner had thrown it in his face like that. So… now what? Did he really believe that Crowley had feelings for him? It was hard to imagine Crowley having feelings for anyone, but… Dean had always found the way he acted towards him to be hard to explain. But even if he did have those feelings, he clearly didn’t want to do anything about them – it would be bad for his image. But he also didn’t want Dean dating anyone else. So… maybe he did want something more?

The questions chased each other around Dean’s mind for a couple of hours, until he finally decided that the only way he was ever going to solve anything was to actually talk to Crowley – something that he had really been hoping he’d be able to avoid. There was nothing like confessing your feelings after a fight that ended with ‘I never cared about you.’

As he walked up the stairs to the bedroom, he wondered what he should do if Crowley was already asleep. Should he wake him up? Or just wait till morning? Would he still have the courage to talk to him in the morning? Would waking him up put him in a bad mood, making the conversation that much harder? He was really getting tired of all the questions.

He pushed the bedroom door open quietly and his heart plummeted down to his stomach. Crowley was indeed asleep, but he wasn’t alone. Curled up next to him was a beautiful, dark-skinned girl with curly, brown hair.

Dean wanted nothing more than to slam the door shut and run from the house. It was the fight or flight response, and he’d been fighting this thing with Crowley for so long, that now he didn’t have any energy left to do anything but flee. But where could he go? Sam was in California, Bobby would want an explanation, he didn’t even know where Benny was living right now, and he had no one else. So, he exercised self-control and stepped backwards, carefully pulling the door shut.

He hated how it felt like someone had punched a hole in his chest, hated that he had opened himself up to the idea of there being something between him and Crowley only for _this_ to happen. He just wanted this whole day to go away, to never have happened. He hadn’t realized just how happy he had been that morning until now.

He did everything he could to shut his emotions off, ignoring the dampness in his eyes as he walked down the hall to the guest bedroom and collapsed into bed, not even bothering to undress. As he tossed and turned, finding it difficult to get comfortable without Crowley there beside him, he deiced that he really shouldn’t be surprised by how everything had turned out. It was just one more thing that he had screwed up spectacularly.


	6. Little Less Miserable

Dean had hoped that he’d have a few moments of peace when he woke up the next morning – just a few seconds before the events of the previous day caught up with him. He had no such luck. It all came rushing at him the second he opened his eyes – the heartache, the regret, the dread of having to face Crowley. It made him want to never leave the bed. But wallowing in his misery had never been his style. He was better off staying busy, distracting himself from whatever was weighing him down. So, he swallowed his self-pity and got up, forcing himself not to think about Crowley or anything else as he got ready and went downstairs.

Of course, it was just his luck that when he walked into the kitchen, Crowley was seated at the small table beside the woman from the previous night.

“Dean.” Crowley raised his eyebrows slightly as he turned from the woman to Dean, the corners of his lips quirking up slightly. “I didn’t expect you to be here. This is my friend, Billie; Billie, this is Dean. I’m providing him housing until he can get back on his feet.”

Billie looked up at him and nodded her head. “Hey.”

Dean barely looked at her, just gave her a curt nod as he walked past the table and started to rummage through the cabinets for some cereal. He didn’t have the energy to cook today.

“It’s been fun, Crowley,” he heard Billie saying behind him. “But I should be off. Lots of work to do.”

“Of course,” Crowley replied, that flirtatious edge to his voice that Dean was used to being directed at him. “Call me if you get bored.”

“Oh, I will.”

Dean gripped the handle of the refrigerator just a bit too tightly as he yanked it open, pulling out the milk as he heard the merciful sound of Billie’s retreating footsteps. He could feel Crowley’s eyes boring a hole into his back as he poured his milk and cereal into a bowl, but he resolutely ignored him.

Crowley waited until Dean had put the box of cereal and the milk away before he spoke. “How was your date?” he asked casually.

“Great,” he answered, trying his best to inject some enthusiasm into his voice.

“Hmm,” he hummed skeptically. “That why you’re waking up here instead of at Gunner’s?”

Dean glared down into his cereal bowl. He really should’ve gone somewhere else last night. “He just… he had something come up.”

“I’m sure he did…. You didn’t seem too happy to see Billie. Is there a problem?”

“Course not.” He spun around to direct his glare at Crowley. “Why would there be?”

“You tell me.” He rose to his feet, taking a step closer to Dean as a smirk spread across his features. “Could it be that, after all your accusation yesterday, _you’re_ the one who’s truly jealous?”

Dean scoffed. “Please. I couldn’t be _less_ jealous.” He forced himself not to cringe. Even _he_ didn’t think he sounded convincing.

Crowley arched an eyebrow at him. “That so?” He stalked forward until he was just a few inches away from Dean, his eyes locked on his. “Then what would you call that bitter, heart-wrenching look in your eyes?”

He ground his teeth together. Of course Crowley would make this into some kind of joke. “I’m moving out,” he blurted out before he even consciously formed the thought.

He blinked, the smirk wiped from his face to be replace with surprise. “What?”

“I’m moving out,” Dean repeated. Even though he hadn’t really thought it through, now that the thought was in his head, he couldn’t shake it. There was no way he could continue living in the same house as Crowley after last night. “Living _and_ working together is just too much. And since I don’t exactly got a choice about the working together part…”

“So, you’re going back to Bobby’s?” Crowley asked slowly, his voice and expression unreadable.

“No. No way he won’t get suspicious. I’ll figure something else out.”

“Right….” He cleared his throat. “Well, if you just stay here until this deal with Abaddon goes through, you’ll receive a decent cut – should be enough to afford yourself a nice place.”

Dean shook his head. “I’m not waiting that long. I’m leaving today.”

Crowley’s eyebrows furrowed in concern. “You can’t. Where will you go?”

He shrugged. “Don’t know. I’ll figure something out.”

He shook his head slightly. “I’ll lend you some money-”

“No way,” Dean cut him off. “I’m not becoming any more indebted to you than I already am. Don’t worry, I can take care of myself. Besides, it’s not like you care, anyway,” he shot at him.

His eyes narrowed. “You bloody moron,” he growled.

He didn’t want to hear it. Was it stupid of him to run off without any idea of where to go? Maybe. Probably. But he couldn’t do this anymore. And he wasn’t about to stand there and listen to Crowley telling him how idiotic he was being. He moved to shove past him, his cereal forgotten, but Crowley gripped his arm tightly and shoved him back into the counter.

“Let me get this straight,” he all but snarled. “You’re running off with _no_ plan, are risking _dying on the streets,_ all because you refuse to admit that you’re jealous?”

Dean’s eyes narrowed, but his voice was deadly calm. “Let go of me, Crowley. Before I make you.”

He scoffed. “Stop choosing battles you can’t win, Dean.”

He snapped. Years of wrestling in high school meant that he knew just how to twist to break Crowley’s grip. Simultaneously, he swung his other fist towards his face, but he ended up being stopped by a hand closing around his wrist and twisting his arm back painfully. He only allowed himself a brief grunt of pain as he reached behind himself, grabbing his bowl of cereal and throwing it at Crowley’s head – it was cheap, but it did the trick, at least for the time being.

Crowley didn’t let him have the upper hand for long. He collected himself in a matter of seconds and managed to grab hold of Dean’s other wrist, twisting both of his arms around to pin his hands behind his back. Dean wasn’t giving up, though; for every hold that Crowley put him in, he got out. But for every punch he threw at Crowley, he managed to block it. Neither of them could manage to hold the upper hand for more than a few seconds.

Some part of Dean knew that this was pointless. He didn’t _really_ want to hurt Crowley, and he wouldn’t gain anything by doing it. But he had had enough. Last night, Crowley had done everything in his power to tear him down, and now that his feelings were evident, the asshole was turning it into a joke. And then he even had the audacity to act like he got a say in his wellbeing! So, since throwing punches was significantly easier than actually dealing with his emotions, so he wasn’t planning on stopping anytime soon.

He eventually managed to get them to the ground, Crowley pinned beneath him.

“This just got a lot more interesting,” Crowley taunted. “Bet you have a lot of pent-up sexual tension, considering _you_ weren’t the one to get laid last night.”

This time, Dean did manage to punch him in the face. He expected that that would be the last straw to get Crowley to do more than merely defend himself, to get him to hit back – and maybe some part of him wanted that – but instead, Crowley just stared up at him, his face expressionless.

“That make you feel better?” he asked calmly. “To hit me like some wild animal, rather than talk about your problems?”

“My only problem is you,” Dean growled.

“Your problem is yourself,” he immediately refuted. “You’re too stubborn and proud to admit the truth.”

“Yeah?” he challenged. “And what’s the truth, then?”

Before Dean knew what was happening, Crowley had rolled him over so that he was now the one pinning Dean down. He opened his mouth to protest, but before he could get anything out, Crowley’s mouth was on his, kissing him fiercely.

All of the fight drained out of Dean as, for the first time, he allowed himself to feel what he had blocked out every other time they had kissed. It was a warmth that started in the pit of his stomach and flowed throughout the rest of his body. It was a feeling of belonging, of hope, of the purest form of joy. But this time it was also tainted with a layer of sorrow.

As Crowley broke the kiss, Dean turned his head away, counting the bits of cereal on the floor as a way to distract himself from what he was feeling.

“Would you just talk to me, Dean?” Crowley asked softly.

He couldn’t stop the bitter laugh from escaping his throat. “What’s the fuckin’ point?”

He sighed exasperatedly. “How about the both of us being a little less miserable?”

That got Dean to look at him again, his eyebrows furrowing slightly as he wondered if the implication was what he hoped it was. He had thought that maybe it was possible last night, but after the way Crowley had acted this morning… “And how exactly will it help with that?” he asked, doing his best to keep his voice level.

His squinted at him. “Fine, I’ll go first – give you an example. I called Billie over last night to get my mind off of you. Your turn.”

He blinked, the words swirling meaninglessly in his head for a couple seconds before they finally sank in. _Oh._ He exhaled a puff of air in surprise, then licked his lips as he tried to figure out what he was supposed to say to that. Well, it was his turn to admit something, wasn’t it? “Gunner thought I talked about you too much. That’s why the date didn’t go anywhere.”

Crowley grinned victoriously. “I do apologize for ruining your date. Guess I’ll just have to take you out to make up for it.”

Dean couldn’t stop the smile from breaking out over his face, the warmth that had come with the kiss washing away the sorrow. “Yeah, I guess you will.”

He rose to his feet and held out a hand to help Dean up. As he did so, his smile softened, becoming more genuine – it was a smile that Dean had never seen on his face before, and he immediately decided that he wanted to see more of it. “Are you free tonight?”

“I don’t know…” he mused as he accepted his help. “My boss gave me this assignment, and he’s kinda a hard-ass.”

“Are you trying to tell me that you aren’t capable enough to handle both?” he questioned, an amused gleam in his eyes.

“Oh, I’m perfectly capable,” he said, his tone teasing. “I just don’t know if it’s worth it.”

“Oh, is that so?” He took a step closer so that their bodies were flush against each other, and he raised his hands to rest on Dean’s hips. “Guess I’ll just have to convince you, then.”

Dean licked his lips. “Yeah. Guess so.”

Crowley backed him into the counter again, but this time he didn’t mind nearly as much. And hey, now he could cross kitchen sex off his bucket list.

“So, tonight?” Crowley purred as they pulled their clothes back on.

“Yeah,” Dean’s tone was casual, but he had a shit-eating grin on his face. “Guess I can manage that.”

“Excellent.” He grabbed him by his shirt and pulled him into a brief kiss. “And I’m assuming – since you’re _so_ busy with work – you won’t have time to date anyone else anymore?”

He smirked as he leaned back against the counter, crossing his arms over his chest. “That what you want?” He knew full well what his answer would be, but he just had to hear him say it.

“…Perhaps,” he allowed, slightly reluctantly. “But you feel the same,” he quickly added.

Dean shrugged. “Yeah. I can admit it.”

Crowley’s expression was a mixture between gratified and curious. “Well, that’s new.”

“Yeah, well, we could’ve had this conversation last night if you hadn’t decided to get back at me with Billie,” he said, some of his earlier bitterness seeping back into his voice.

“What makes you think I slept with her to get back at you?” he demanded.

“You gonna tell me you didn’t?” he challenged.

“No,” Crowley admitted unabashedly. “Don’t know where you got the idea, though.”

Dean rolled his eyes. “You always have to have the last word – that was your way of ensuring that.”

“Well. Color me impressed.”

“I generally do when you’re around me,” he teased, for the first time conscious of the fact that he was actually flirting with Crowley.

“If that makes you feel better, darling, you can imagine whatever you want,” he retorted smoothly.

“Hmm…. Well, I can imagine quite a few things involving you.” He waggled his eyebrows.

Crowley smirked. “Oh, likewise. You want to hear one?”

He pursed his lips thoughtfully. “I’m not gonna say no.”

“Well…” He leaned in close, his voice pitched low. “Right now, I would just _love_ to see you… clean up your bloody mess.”

Dean glared at him as he took a step back.

“Now, I’m going to go take care of Juliet, and I do hope my fantasy will become a reality.” Before Dean could say anything, he turned and walked out the door.

He rolled his eyes at his retreating frame. He supposed that _was_ fair, since he had thrown a bowl of cereal at him. He grabbed a broom and dustpan from the closet and set to cleaning up the mess, his mind reeling from what had just happened.

He was going on a _date_ with _Crowley_ tonight. That wasn’t something he would have ever thought would happen – and before yesterday, he would have insisted that he hated the very idea of it. But now that it was reality, he didn’t feel the same frenzied nerves that he’d felt in middle school talking to his crush, like he had felt after securing a date with Gunner. No, there were definitely still nerves, but there was a certain… comfort that laid over them like a blanket, making them more of a dull hum in the background. This wasn’t a date with some celebrity crush, this was a date with a real person that he had an honest connection with – something that he’d never thought he’d find, really. Whatever misgivings he might still have about dating Crowley – and there were certainly still plenty of those – he couldn’t deny that this felt _right._


	7. Airborne

“Hello… Cecily? My name’s James Hetfield. I understand that you used to work for Abaddon?”

Dean could hear the confusion in Cecily’s voice as she responded. “Yes… but that was like five years ago.”

“I understand that,” Dean assured her. “My company is looking into a partnership with hers, and I like to do thorough research into anyone I’m thinking about partnering with, just to be sure I won’t be in for any nasty surprises. I’m sure you understand.”

“Oh, yes. So, what do you want to know?”

“How was she to work for?” he asked, deciding it would be best to start out simple.

“I mean… I thought she could be a little harsh sometimes, but she got the job done,” she explained hesitantly. “The company did great under her management.”

Dean could translate that easily enough: She was good at the work, but she didn’t care about her employees. Not that that was anything he didn’t already know. “Yes, and I’m glad you mentioned that,” he said, leaning back in his chair. “Given how well the company was doing, I can’t help but wonder why she left.”

“I think that had more to do with her moving than leaving the company itself.”

“Right, this was her last job in Missouri, wasn’t it?” he asked as though he had only just remembered. “Do you know why she moved?” He was careful to keep his voice only casually curious.

“Well… there was quite a bit of gossip…”

Bingo. He could hear it in Cecily’s voice that she wanted to say more, but she wasn’t sure if she should. “Everything you say stays between you and me,” he assured her.

“Okay, well, she’d had this long-term boyfriend,” she jumped in. “And they were actually partners in the company. Then one day, he just… left. No explanation. Abaddon was _pissed._ Most people assumed that they broke up, so he didn’t want to work with her anymore. But she kept trying to push him to come back – she was the ‘we’re not over until I say we’re over’ type. Of course, he never came back, and Abaddon kept running the company on her own for a couple years. It was shortly after I noticed a _certain someone’s_ marriage announcement in the paper that she started arranging for me to take over the company.”

“Wow. So, you think it was all because of this guy?” Dean asked, finding that a little hard to believe from what he knew about Abaddon.

“Yeah. I mean, I never would’ve thought she’d be so soft, but…”

“But people can surprise you,” he finished for her with a small smile. He knew all about that. He still wasn’t covninced that Abaddon moved because of a broken heart, but it was a start, at least. “Hey, do you have his info? It could be good to talk to someone who worked side-by-side with her.”

He wrote down the name she gave him, feeling quite satisfied with the day’s work. “Thanks, Cecily. You’ve been a great help.”

He put down his phone, turning his attention to the office doorway, where Crowley was leaning against the frame. “So, just because we’re dating now, you think you have a right to make yourself at home in my office?” he demanded, but his tone was light.

Dean rolled his eyes. “Not sure you can call it ‘dating’ when we haven’t actually been on that date yet. And you do want me to do my job, don’t you?”

“Of course.” He pushed off the frame as he walked into the office. “You get anything?”

“She has an ex back in Missouri,” he said, picking up the piece of paper in front of him and waving it. “I have a good feeling he’ll have some dirt on her.”

“All in a day’s work,” he praised with a satisfied grin. “Not bad.”

“Haven’t done anything yet – still have to track this guy down and convince him to spill.”

“Which I am utterly confident you will do.”

Dean grinned, feeling more at ease purely from Crowley’s confidence in him. “Thanks, Crowley.”

Crowley walked closer so that he could lean down and peck Dean on the lips. “Don’t you have a date to be getting ready for?”

“Yeah, I guess I-” He was cut off by his phone ringing, the name ‘Bobby’ flashing on the screen. “Hold that thought.” He answered his phone bringing it to his ear. “Hey, Bobby, what’s goin’ on?”

“You tell me, ya’ idjit,” Bobby replied gruffly. “I haven’t heard from you in a week. You said you’d keep in touch.”

“Uh, yeah, sorry, Bobby,” he sighed, running a hand over his face. “Just been busy, what with starting the new job and-”

“Yeah, I’m sure you don’t have a spare second to let me know you’re doing alright.”

“Well, I… I’m sorry. I should’ve called.”

“Damn right. Now,” his voice abruptly softened (as much as Bobby’s voice ever did), “how about you come over for dinner tonight? I’m grilling up some burgers, I thought we could watch a movie or somethin’.”

“That sounds great,” Dean said guiltily. “But… I kinda have a date.”

“A date? Who with?”

“Just… this girl I met at a bar. Nothing serious,” he added to stop any further questions.

“Well, alright,” he sighed. “I expect you over sometime soon, though.”

“Course,” he muttered, knowing full well he’d do everything in his power to avoid that. It wasn’t that he didn’t want to see Bobby, because he did, he just knew that lying to his face would be a lot harder than lying over the phone. “Well, I gotta be going. Talk to you later, Bobby.”

“Yeah. See ya, Dean.”

Dean hung up the phone with a sigh. These lies were going to get really old really fast.

“Nothing serious?” Crowley’s voice pulled him from his thoughts. “You wound me.”

“You’ll get over it,” he shot back with a grin.

He returned the grin briefly, but then it faded. “I can’t help but notice you said ‘girl.’ Does he know…?”

Dean sighed, shaking his head. “No. He doesn’t.”

“Why not?”

He shrugged, not quite looking at him. “I dunno. It’s not that think he would judge me or anything like that…. I guess was just always worried that it’d get back to Dad somehow. Sam was the only one in the family I felt safe knowing – not that I even had a choice there, he called me out on it before I could psych myself up to tell him.” The ghost of a fond smile flickered across his face briefly. “But with Bobby, I just don’t know how to tell him after keeping it secret for so long. Like, ‘Hey, I’ve been out of the closet with everyone except you for years. Just so you know.’” He shook his head, letting out a humorless laugh. “Besides, I’m keeping so much from him these day, it almost makes sense to keep this secret, too. What’s one more thing, right?”

Crowley sat down on the edge of the desk, his gaze sympathetic. “You know, you could always tell him partial truths. Sam, too.”

He shook his head. “No way. Sam’s already met you, and he trusts you just about as much as I did when we met. And Bobby won’t be any different. They’ll ask too many questions.”

He shrugged. “Your family, your call.”

“Damn right it is,” he agreed as he got to his feet, giving Crowley a quick kiss on the way up. “Guess I’d better go get ready for our date. Don’t suppose you’ll tell me what we’re doing?”

“That’s why it’s called a surprise, darling.”

* * *

 

“A… that’s a helicopter,” Dean stammered out, staring at the craft before him.

“It is,” Crowley said proudly. “I borrowed it from an associate – thought we could take the scenic route to our destination.”

“Oh,” he said weakly. “That… that’s…” He swallowed thickly.

He turned to look at him, his brows furrowed. “What’s wrong?”

Like hell was he telling Crowley the truth, he would never hear the end of it. “Nothing,” he denied, his voice shooting up slightly. “Nothing. Let – let’s do this.”

Crowley studied his face carefully for a second before an amused smile quirked up the corners of his lips. “Are you afraid of flying?”

“No, I just…” He tried to come up with a plausible excuse as to why he was freaking out at the prospect of getting in a helicopter. “It doesn’t look very safe to me.”

He arched an eyebrow, glancing between him and the shiny, new helicopter in front of them. “It’s almost brand new, Dean. It’s perfectly safe.”

“Right. Well, um… okay, _fine,”_ he snapped, relenting. “I’m afraid of flying. Happy?”

To Crowley’s credit, he did _try_ not to laugh. “The big, brave Dean Winchester is afraid of flying?”

“Shut up!” He crossed his arms over his chest as he turned away from him, glaring at the building to his right.

“Okay, I’m sorry. I was just under the impression that you weren’t afraid of anything.”

He gave an incomprehensible grumble in reply. Well, this was the most embarrassing first date ever – which was really saying something after how his date with Gunner had gone.

“We can drive there,” Crowley offered. “It’ll take us a bit longer, but we’ll make do.”

Yeah, and then Dean would never hear the end of it. He absolutely did _not_ want to get in that helicopter, but even more so, he also didn’t want to seem like a complete coward. “Get in the damn helicopter,” he spat as he started stalking forward.

“Dean,” he protested grabbing hold of his arm. “You don’t have to prove anything to me, you know.”

“I’m not trying to,” he insisted. “I just… want to enjoy the date you planned for us.”

“You’re sure…?”

“Yep. Let’s go.”

Dean might have been holding on for dear life and humming Metallica the entire flight, but he was able to make it without getting sick or passing out. He considered that a win.

“You alright?” Crowley asked when they reached their destination.

“Yeah, just… give me a minute,” he muttered, allowing his head to rock back against the seat.

“I’ll call us a car for the return trip.”

Dean gave him a thumbs-up. A minute later, his stomach stopped churning enough that he was finally able to relax enough to look outside and take in their surroundings. They were walking distance from a lake, and he could just make out a boat docked nearby. “Where are we?” he asked as he took off his headset.

“See for yourself,” Crowley said as he hopped out of the helicopter and walked around to open the door for him.

He stepped down and fell into step beside Crowley as he led him towards the lake.

“I hope you’re better with boats than you are with helicopters,” he commented as they got close enough that Dean could see the small yacht that they were approaching.

Dean let out a small, disbelieving laugh. “Yeah, I’m good with boats.”

Crowley looked at him out of the corner of his eyes. “What is it?”

He shook his head slightly. “This is just… a lot.” A helicopter ride to a freakin’ _yacht?_ This wasn’t the type of date Dean went on – he went to dive bars and diners, maybe a halfway decent restaurant if he was splurging… he wasn’t quite sure how to handle this.

“To much?” he asked, a worried frown pulling down the corners of his lips slightly.

He shook his head. “No. This is amazing, Crowley.” _I just don’t deserve it,_ he finished in his head.

“Good.” He led him onto the boat, and then set to untying it from the dock. Shortly after he was finished, the yacht started to move.

“You borrow this from an associate, too?” Dean asked as he leaned against the rail, watching the scenery as they moved.

“No, this is mine,” he said with a casual shrug. “I just had to hire the driver.” He stepped up beside him, wrapping an arm around his waist.

“Damn,” he breathed. “Didn’t realize you’d be showing off so much.”

“I’m not showing off,” Crowley protested, a mildly offended note in his voice. “I just want to spoil you.”

Dean turned to face him in surprise. “Why?” he asked blankly.

He blinked. “Because… you deserve it.”

 _Yeah right,_ he thought harshly.

He took a deep breath. “But also because… I know I hurt you, Dean. And I’m used to hurting people, I couldn’t care less most of the time. So… I was surprised by how bad I felt when I saw the look in your eyes yesterday – and then again this morning. I suppose I’m trying to make up for that.”

Dean nodded. That made a little more sense, he supposed. “Well… I gotta admit, this is one hell of a start.”

Crowley smiled. “Hungry?”

“You know me.”

He led him up to the top deck, where a table for two had been set up, complete with candle light and a platter of delicious-looking seafood.

“So, who catered?” Dean asked with a smirk as he took his seat.

“Maritime Grill,” he admitted as he sat down across from him. “I did make dessert, though.”

“Pie?”

“Pie.”

“You’re awesome,” he said as he started helping himself to the platter.

“Are you really so surprised by all this?” Crowley asked a few minutes later, gesturing around them with his hand.

“Yeah,” Dean said, thinking that should be obvious. “I didn’t really think you were the dating type. And this is… so beyond any date I’ve ever been on.”

“Well, that’s the point,” he said immediately. “I’m not the dating type in the slightest, so if I’m going to start dating, I might as well go all out.”

He chuckled. “I must be pretty special if I’m getting you to date,” he teased.

“You are,” he said solemnly, his expression completely serious.

Dean swallowed uncomfortably and turned his attention back to his food. Compliments weren’t really something that he knew how to deal with, but he had a sinking suspicion that Crowley had a lot more where that came from. This dating seriously thing was definitely going to take some getting used to. If how much he enjoyed the rest of their date was anything to go by, though; it was totally worth it.


	8. Road Trip

“You sure I have to protect Purgatory’s little angel?” Crowley grumbled as he walked into the kitchen, having just gotten home from work.

Dean rolled his eyes as he turned from the stove. “‘Little angel’?” he repeated with a wry grin. “Really?”

He shrugged. “It’s what all the other guards call him. Don’t tell me you can’t see it.”

He chuckled. “Well, Cas is definitely more angelic than you, that’s for sure. Not that that’s saying much.” He winked before returning his attention to stirring the spaghetti sauce. “What’d he do?”

Crowley sighed as he sank into one of the kitchen chairs. “Ever since you came through the prison, he’s become even more suspicious of me than usual. My good mood today damn near prompted an interrogation.”

Dean found himself smirking slightly. So, Crowley had been in such a good mood the day after their date that even Castiel could tell? That was good to know. “I’m sure the black eye helped,” he teased. Crowley had indeed woken up that morning with a black eye from where Dean had punched him the previous day.

“Oh, yes,” he said, his voice heavy with sarcasm. “It’s far easier to explain away a good mood when sporting a black eye.”

“I am sorry about that,” he said apologetically.

“I’ve had worse,” he brushed it off, much like he had that morning when Dean had freaked out upon seeing it. “But if anyone asks, it happened at the prison. Can’t have people thinking my second roughed me up and got away with it.”

“Well, if it’s any consolation, I didn’t get away entirely unscathed. I’m pretty sore from last night.” He threw him a grin over his shoulder.

That got Crowley to perk up slightly. “It is, indeed.”

“Good.” He reached over to turn off the stove. “Dinner’s ready.”

After they had dished up and taken their seats at the table, Dean couldn’t help but notice that Crowley still wasn’t his usual overly-confident self. He kicked him gently under the table. “What is it?”

He gave a small sigh. “I’m worried that Castiel will cause problems,” he admitted. “I think he suspects that I had something to do with getting you out of prison.”

“Okay, well, it’s not like he’d be pissed about that. He’s my friend.”

“But if he thinks your freedom came at a price-”

“Which it did,” Dean pointed out.

Crowley gave him an indignant look.

“Hey, it did!”

“You’re not helping.” He shook his head. _“Anyway,_ regardless of the benefit to you, he would jump at the chance to get me fired.”

He didn’t want to admit it, but he knew Crowley was right. Castiel wanted nothing more than to purge the injustice from the prison that his brother had corrupted, and it wouldn’t matter to him that there was far worse than Crowley there, if it meant making what little difference he could. “He’s my friend, Crowley,” was all he could say. “He’s done a lot for me.”

“I know,” he sighed. “I just hope you realize how difficult it is protecting someone’s job when he wants _me_ fired.”

Dean reached out, taking Crowley’s hand in his. “Thank you,” he said fervently.

Crowley scowled slightly. “You’re lucky it’s near impossible to say no to you.”

“Well, hopefully that will come in handy.” He squeezed his hand slightly before he pulled back.

He nodded. “You all packed?”

“Ready to leave first thing in the morning,” he confirmed. He had called Crowley during his lunch break, letting him know that he’d managed to track down Abaddon’s former lover, and that he thought it would be best to pay him a visit. “You gonna be alright without me?”

He rolled his eyes. “I think I’ll manage.”

“Well, as long as you manage on your own,” he muttered, looking down at his plate. “Not with the help of Billie, or Gabriel, or… whoever else.” He _thought_ that wouldn’t be an issue, but he still wasn’t entirely sure where they stood now, to be honest.

“Dean.” Crowley’s voice was soft with an earnest undertone that prompted Dean to look up, meeting his gaze. “You said it yourself – I only slept with her to get back at you. And everyone else, I cut ties with back when we first started sleeping together.”

“Seriously?” Dean raised a skeptical eyebrow. “Even back when I was in prison?”

He gave a small shrug, his gaze drifting away from Dean’s. “Guess it meant more to me than it did to you.”

Well, that felt like a punch to the gut. Not that he could blame him for feeling that way – he had always advertised that his opinion of Crowley was pretty low, even when it had started getting harder to lie to himself about it. “Hey, don’t – don’t think that,” he forced himself to say, despite his instinct to hide his vulnerability. “You meant something to me, too… I just didn’t want to admit it,” he muttered, his gaze flickering away.

“And you think it was easy for me?” he questioned. “I’m supposed to have a cold heart, remember?”

“Hard to forget. You sell the façade well.”

“It’s not a façade,” he protested indignantly.

Dean arched an eyebrow at him. “So, what do you call this?” he asked, motioning between the two of them.

“An exception.”

He rolled his eyes. “Right. Whatever makes you feel better. Though why you _want_ to be a cold-hearted bastard, I’ve got no idea.”

“It’s better for business,” he said smoothly.

“I do just fine,” he pointed out. “I’m not a bastard.”

“My black eye says differently,” he teased. “Also, most of the team doesn’t trust you.”

“Well, if all goes well tomorrow, that’s about to change.”

“And it will,” Crowley said confidently. “You can sweet talk your way into anyone’s circle of trust.”

“Oh, so now you’re encouraging me to sweet talk other men?” Dean joked.

“Professional sweet talk. It’s different.”

He laughed. “Professional sweet talk. That something I can list on my resume?”

“Certainly,” he said with a slight smirk. “Right next to blackmail.”

Dean’s amused smile slipped slightly. “…Right.” Yeah, maybe he did enjoy working with Crowley, but that didn’t mean he wasn’t still morally against what they were doing. Not that he’d been a strictly law-abiding citizen, even before he had killed a guy, but this business still sat uneasy with him.

The look in Crowley’s eyes shifted into something that was hard to define – something between concerned and… sad? “Dean, if you…” he trailed off, looking down at his plate.

“What?” he pressed.

He cleared his throat. When he looked up, his expression was more relaxed, but it didn’t quite reach his eyes. “If you would like some advice for how to handle things tomorrow, I’m all yours tonight.”

Dean got the distinct impression that that wasn’t what he had been about to say, but he decided not to push it. He gave Crowley a devilish grin. “Well, if you’re all mine, I can think of far better things to do than getting advice.”

* * *

 

Given how much Dean had dreaded moving in with Crowley in the first place, he wasn’t expecting how difficult it would be to leave for just a couple of days. But then again, a lot had happened that he hadn’t been expecting. The drive to Missouri felt good, though; there was something serene about steering his Baby down the road that wound before him. It certainly helped to ease his nerves over how everything was about to go down.

Too soon, he came to the address that he had tracked down, and the peace that being on the road had brought him dissipated. If he were the praying type, he would be praying now… but something told him that God wouldn’t be helping him with this, anyway.

He took a deep breath as he got out of the car and made his way to the door, knocking twice before stepping back and listening to the approaching footsteps.

The door was pulled open by a well-built man with graying hair and beard, his eyes sharp and calculating as they landed on Dean. “Who are you, and what are you doing here?” he demanded.

Dean pulled his most charming smile. “Are you Cain?”          

His eyes narrowed slightly. “I repeat my question.”

Okay, so not big on pleasantries, then. “I’m James Hetfield. I’m in the midst of negotiating a partnership with your former business partner, and I was hoping-”

“You’re lying,” he cut him off, his tone matter-of-fact. “You coming onto my property uninvited is one thing, Dean Winchester, but now you’re wasting my time with lies?”

Dean felt frozen to the spot, his mouth going dry. _Crap._ “No, my name’s James-” he tried desperately to save himself, but he was interrupted again.

“James Hetfield is the lead guitarist of Metallica. _You_ are the man who killed Dick Roman.”


	9. Let's Make a Deal

Cain took a step backwards, allowing room to get past him, into the house. “Come on in, Dean.”

Dean hesitated, but the way he saw it, he really didn’t have a choice. He needed information from him, and yeah, it was definitely risky as hell, but what else could he do? He stepped into the house cautiously, and the door was closed behind him with a finality that could have just been his imagination, but it made him nervous all the same.

“Would you like some tea?” Cain asked casually as he walked past him, further into the house.

“Um… sure?” he responded, slightly disconcerted. Honestly, he could go without tea, but he didn’t really feel like he could refuse. Any chance he had had to maintain a modicum of control over this conversation had gone out the window entirely, leaving Dean having to suppress his fight or flight response.

“Have a seat.” He motioned towards the living room while he proceeded to what Dean presumed to be the kitchen.

Dean stood there for a second, still trying to come to grips with what was going on, before he turned into the living room and gingerly took a seat on the couch. He cast his gaze around the room as he waited – the décor was fairly simple, definitely closer to the kind of place that he had grown up in than where he was living now. With that thought came a sudden, unbidden desire to have Crowley there with him. He’d probably know just what to say to Cain to turn the situation back in their favor – not that he’d ever confess any of this to his face, of course.

“I hope you don’t mind, I added a little bit of honey,” Cain said as he entered the room, carrying a tray with a couple of teacups on it. “I collect it myself.”

Dean’s eyebrows furrowed slightly as he reached forward to take one of the cups. Whatever he had expected from Abaddon’s ex, it certainly wasn’t this. “Thanks,” he said, nevertheless.

He nodded as he set down the tray on the table and then took a seat in the chair across from Dean. “So, what are you really doing here, Dean?” he asked conversationally.

To buy himself some time, he took a sip of his tea. He wasn’t really a tea drinker, but it wasn’t bad, he supposed. “First, I gotta ask, how do you know who I am?” It would help to know what he was working with here.

“Really?” Cain raised an eyebrow at him. “Dick Roman wasn’t just known in Kansas, you know. You kill a figure as notable as him, you’re going to end up on the news.”

Dammit, he hadn’t even considered that. “Right…” he muttered.

“So, I ask again. Why are you really here?”

Dean sighed. His best option was probably just to go with the truth. At least, a partial truth, that was. “I’m sure you’ve seen on the news the real reason I killed Roman. But I know he’s not the only big-name in town committing atrocities. I want to try to bring them down before what happened to me and my brother happens to anyone else. Starting with Abaddon.” If Cecily’s information was anything to go by, the two of them were _not_ amiable exes. Or at least, that’s what he hoped.

“Hm.” Cain eyed him for several seconds, his face expressionless. “Well, you certainly have an eye for the corrupt,” he finally said. “Abaddon makes Roman look like an altruist.”

“But I can’t find any dirt on her,” he continued hopefully.

“No. You wouldn’t. She’s too good at what she does for that.” He stood from his chair. “I can’t help you, Dean. You know the way out.” He started to turn away, but Dean sprang to his feet, setting his teacup back down on the tray along the way.

“Woah, hold on. You just said that Abaddon’s one of the worst there is, and you’re not going to give me _anything?”_

Cain turned back to meet his eyes, his gaze dark. “Exactly. I don’t know what you think you know about Abaddon and me, but I assure you, it’s more complicated than that. You’d be better off staying far away from all of this.”

“Yeah, well, that ain’t gonna work for me,” he protested vehemently, taking a step forward. “Abaddon could be destroying lives-”

“And she probably is,” he interrupted calmly. “But currently, that life is not yours. I suggest you keep it that way.”

It was like an alarm bell went off in Dean’s head. So, Abaddon destroyed his life, then _._ That had to be why he was playing up the whole ‘Stay away!’ act. He thought back to what Cecily had said, _‘But she kept trying to push him to come back – she was the ‘we’re not over until I say we’re over’ type…. It was shortly after I noticed a certain someone’s marriage announcement in the paper that she started arranging for me to take over the company.’_ Oh, shit. If he was right, it would definitely give him something to grasp onto that could get Cain to come around, but he kind of hoped that he was wrong. “Cain… where’s your wife?”

Cain didn’t move, but his jaw clenched slightly, and something flickered in his eyes almost too fast to see – if Dean had to guess, though, he’d say it was sorrow. “Like I said. You best walk away from all this before the life that’s destroyed is yours.”

He should walk away. Whatever had gone down, it wasn’t good. And truth be told, he wasn’t entirely certain that that last warning hadn’t really been intended as a threat. But he had a job to do. Also, he had to admit, he was a little curious as to what made this bitch so terrible. So, he met Cain’s eyes with a level gaze and crossed his arms over his chest. “I ain’t going anywhere until you give me some answers.”

“Is that so?” His eyes narrowed as he scrutinized Dean. “And what do you think gives you the right to demand answers from me?”

“Because I’m trying to do some good here.” If only that were the truth.

His lips curled up into an amused smile that didn’t exactly give off the most pleasant vibe. “And what if I’m not good?”

Dean thought fast. “Hey, I’m no angel, either. But I imagine that bringing down Abaddon is something you want even more than I do.”

Silence for another second. “You really think you can achieve that?”

He smiled confidently. “She wouldn’t be the first.”

Cain nodded thoughtfully. “Then I should probably make us some lunch. It’s a long story.”

* * *

 

“So, Dean, where do you want me to start?” Cain asked about a half hour later as they sat at his kitchen table, bowls of stew in front of them.

“How about at the beginning?” Dean suggested before taking a bite. It was pretty good.

“The beginning….” He looked thoughtful as he took a minute to eat, clearly thinking of what to say. Dean took the moment to pull his cell phone out beneath the table and start a recording. “Abaddon and I had been friends since high school – we’d run with the same crowd back then. When me and… one of our other friends had a falling out, she stood by me. We realized that when we put our heads together, we were unstoppable, and we used that, not for good, but for our own, selfish gain.

“We started a business together, and we were ruthless. We didn’t care what lines we crossed to get ahead. Funny enough, it was through that work that I met Colette.” There was fondness tinged with grief in his eyes as he said the name. “From the moment she walked through the door, there was just something about her that I couldn’t name, and I knew I couldn’t screw her over like I did everyone else.

“There had never been any emotion between Abaddon and me – it was all just about power and sex. Colette, though… she knew who I was… what I had done. She loved me unconditionally. She forgave me. She only asked for one thing. So, I turned my back on Abaddon, on the business that we had built together, and I started a life with her.”

Wow. To love someone so much to walk away from a corrupt life…. Dean quickly shoved the thought aside. That was definitely _not_ something that he needed to think about. There was no way that Crowley would ever…. And that was okay. He was perfectly content with what they had, and he knew full well that love very well may never come from it. He stomped the thought out before he could get too carried away.

“We were happy, for a short while,” Cain continued, oblivious to the direction that Dean’s thoughts had taken. “But Abaddon never forgave me for walking away.” He took a deep breath. “She said that if she couldn’t have me, no one could. So, she killed her. Made it look like the perfect accident, but I knew better. Not that it made any difference.” He met Dean’s gaze again, a bitter smile on his face. “So, that’s my story. Any questions?”

For a couple seconds, all Dean could do was stare at Cain in shock, shaking his head slightly. “Abaddon killed your wife – why did you never do anything about it?” Hell, his dad had made a deal with Crowley to get the information he needed to put Azazel away for Mary’s death. Of course, it wasn’t like _that_ hadn’t had any horrible consequences, but still.

“Abaddon’s good. She was sure not to leave any evidence that could be used against her.” His gaze slid to the side, seemingly focusing on something far away. “Of course, I had other options. But those involved making compromises that I had promised Colette I would never make again. I couldn’t betray her like that, not even to avenge her.”

He could understand that, but at the same time, he wasn’t sure that he’d be able to be as strong, if he were in Cain’s shoes. “Don’t worry. I’ll take her down.”

“With what?” he demanded. “All you have is my word, Dean. And with my record, that doesn’t mean squat.”

Dean’s eyebrows furrowed slightly. “What do you mean, with your record? No charges were ever brought against your company.” Unfortunately. That would make this job a lot easier.

“That’s not what I’m talking about. And it’s not important. The only solid evidence I have against Abaddon pertains to business exploits. Meaning-”

“It’s evidence against you, too,” he finished for him with a sigh. Well, that was just great. Of course, it wasn’t as though getting Abaddon arrested had ever been his plan…. “What if I promise not to take this to the cops,” he implored, leaning forward slightly. “Whatever you can give me – I’ll only use it to keep her in check.”

Cain leaned back in his chair, his face expressionless. “You’re talking blackmail.”

“Your hands will be clean,” he quickly pointed out, seeing where this could go wrong. “I know it’s not ideal, but it’s our only option.”

He was silent for a minute as he thought it over, and then he sighed. “You remind me of myself, Dean. I suggest you be careful, before you cross a line you can’t come back from.”

Dean wasn’t quite sure how to take that, so he brushed it aside, focusing instead on Cain’s resigned tone and the fact that his protesting had ceased. “So, do we have a deal?”

He just looked at him for a couple more seconds before slowly nodding. “We have a deal.”


	10. Catching Up

**Notes for the Chapter:**

> Sorry this took so long. I started a new job, I'm moving in a week, and I'm in the middle of planning my wedding, so life has been a little crazy. I'll try to get the next chapter up in a reasonable amount of time.

Crowley working two jobs definitely sucked. Dean barely had enough time to brag to him about a job well done before he was giving him a swift kiss, and then rushing out the door to get to the prison on time. Even though it had just been a day that they’d been away from each other, Dean had been hoping for a bit more time with him before he had to run off.

He sighed as he sat down behind Crowley’s desk and set to transferring his recording to the computer and filing the records that he had gotten from Cain. The organization’s next meeting was in a couple of days, and he’d present what he’d found then – with the exception of the recording, that was. The rest of the organization didn’t need to know the details of Cain’s past, and if he was being perfectly honest with himself, he felt a little uncomfortable with the idea of listening to Cain talk about what he gave up for Colette with Crowley sitting right next to him. He couldn’t explain why exactly he thought it would be so awkward, he just knew that Crowley was bound to look at him, and he didn’t trust his expression not to be wistful.

He was just finishing up when the door that he had left ajar was pushed open. “Hey, Juliet,” he greeted, looking up as the black pit bull walked around the desk to rest her head on Dean’s knee. He found himself grinning slightly as he scratched behind her ear. Ever since he and Crowley had started… whatever they were doing, Juliet had warmed up to him. If he didn’t know better, he’d think that she was able to tell that there was significantly less animosity between himself and her owner. But surely a dog wouldn’t be able to tell something like that. Juliet did seem to be pretty smart, though….

He sat there petting her, for once glad that he had some company while Crowley was gone. But there was only so much a dog could help with loneliness. Realizing just how much he could do with some human company, he picked up his phone and scrolled through his contacts until he found the one he wanted to call.

“Hello?” the familiar voice answered on the second ring.

“Hey, Benny,” Dean said with a smile. “How’s it going?”

“It’s goin’ alright,” he sighed. “You hangin’ in there?”

“Oh, yeah. I’m doing just fine,” he assured him. “Got some free time on my hands, though. Was wondering if you might like to come out?”

“To Crowley’s place?” Benny clarified, a note of disbelief in his voice.

“My place too, now. I have the right to invite over whoever I like.” Okay, so he and Crowley had never actually discussed it, but he was a grown man living with his… whatever the hell Crowley was to him – he didn’t have to ask permission to invite a friend over.

“I didn’t realize you were makin’ yourself at home. I thought it was a temporary fix. What’s wrong? Crowley holding back your pay, so he can get more action?”

Dean felt his cheeks heating up slightly. “It’s… kinda complicated….”

“Well, I look forward to hearing all about it when I get there. Send me the address?”

“Will do.” As he hung up the phone and typed out the address to text to Benny, he wondered if he had thought this through. Benny was the one person who – after his life had become an intricate web of secrets and lies – he had always been completely honest with. And it wasn’t that he felt that he couldn’t tell him what was going on between himself and Crowley, it was more that he wasn’t entirely sure of what _was_ going on between them. Sure, they were dating exclusively now, but he wasn’t sure if he could classify them as actually being in a relationship – mostly because the very notion of Crowley being in a relationship made him want to laugh. And as for himself, well… did he even _want_ to be in a relationship?

He shook his head. Now was not the time to speculate about things that would more than likely never happen. He’d just have to dismiss any questions that came up today, and Benny could deal with it.

Since it would take Benny some time to get there, Dean decided to check in with Sam while he waited – a decision he immediately regretted after he spent the entire phone call feeding his brother lies and excuses. He really needed to do some damage control with Bobby, since he was apparently calling to gossip about him with Sam whenever he couldn’t get hold of him.

“Honestly, everything’s fine,” he repeated for the fifth time. “It's just been an adjustment period.”

“So, you didn't… don’t take this the wrong way, Dean, but you didn’t get involved in anything… illegal while you were in prison, did you?” Sam asked hesitantly. Sometimes he really hated how smart his brother was.

“What? I kill two guys, and suddenly you think I’m some kind of criminal?” he attempted to brush it off as a joke.

“I’m being serious.”

“Me too! From the bottom of my heart, the worst crime I've ever committed is murder.” Hey, it was the truth.

Sam sighed. “Fine. But if anything's going on, you know you can talk to me about it, right?”

“Yeah, I know that, Sammy,” he sighed, all jokiness leaving his voice. He cleared his throat. “Well, I gotta be going. Benny's on his way over.”

“Your friend from prison?” he asked, his voice going flat.

He sighed. Not this again. “Yes, the _reformed_ pirate. Honestly, he’s probably a better guy than I am.”

“I doubt that. I don’t trust him.”

“You’ve never even met him!” he exclaimed, shaking his head. “Look, he looked out for me in prison, he’s a good friend to me, and I’m not having this argument with you again.”

“Dean-”

“Gotta go. Bye.” He hung up the phone before Sam could say anything else. What was his relationship with his brother coming to when the one thing that he was honest with him about, they argued over every time it was brought up?

Thankfully, he didn’t have to dwell on his deteriorating relationship with his only family for long, because the buzzer sounded to inform him that someone was at the gate. With a feeling of relief, he let Benny onto the property, then opened the front door to greet him.

“I knew Crowley had money,” Benny said as he walked up the front steps. “But damn.”

“Tell me about it,” Dean chuckled, pulling his best friend into a hug when he got close enough.

“It's good to see you, brother.”

“You too.” He clapped him on the shoulder as he pulled back, then stepped aside to allow him to enter the house.

Almost as soon as Benny crossed the threshold, he was greeted by a growl, and Dean turned to see Juliet standing at the foot of the stairs, staring down the new arrival.

“Juliet,” he quickly captured her attention. “It’s okay, girl. He’s a friend.” He placed a hand on Benny’s shoulder to demonstrate his point. The dog didn’t seem to be any more at ease, but at least she stopped growling. He rolled his eyes. “Pretty sure she needs Crowley's approval before she trusts anyone.”

Benny chuckled. “Well, your approval clearly means somethin’. Didn’t realize you and Crowley owned a dog together.”

Dean felt his cheeks heating up slightly. “We don’t. She’s all his,” he quickly corrected. “She’s just gotten used to me. She hated me at first, believe me.” He reached out to scratch Juliet behind the ear as she walked up to him.

“Sure looks like it.” He looked Dean up and down, his gaze scrutinizing. “I take it quite a bit has changed since Purgatory.”

“Uh…” He rubbed the back of his neck uncomfortably. “Maybe a little, I guess. You know, new job and all…”

“Yeah, how is it workin’ for the devil?”

Dean rolled his eyes. “Crowley’s not the devil, and… it’s not so bad. You want something to drink?” he quickly changed the subject, starting down the hall

“Yeah…” Benny’s voice had a definite note of curiosity in it, but he didn’t press it as he followed him into the kitchen.

Dean grabbed a couple of beers out of the fridge and carried them over to the table, setting them down before taking a seat himself.

Benny's gaze was back to being calculating as he sat down across from him and took a long drink of his beer. “So, you and Crowley stepping on each other’s toes yet?” he asked casually.

“Yeah… a bit,” he hedged because they _had._

“Hm.” He took another drink without looking away, and Dean couldn’t help but feel like he was back in the courtroom being drilled by the prosecutor. “Well, if you need a place to go, my bed’s always open.” He threw him a wink.

Dean coughed awkwardly. “Uh… I think I’m gonna have to pass you up on that.”

“Oh, so you _don't_ want to get out of here?” he questioned, the corners of his lips curling up in victory.

“No – I mean, I… it’s convenient. Living here.”

“And the sex is good,” Benny added with a knowing smirk.

“The sex is _amazing._ Not that it wouldn’t be amazing living with you,” he added quickly.

“Relax, chief,” he chucked. “I know you and Crowley have somethin’ special.”

“What?” Dean sputtered. “We don't… I mean, where would you even get that?”

He rolled his eyes. “I saw you two in prison, I can only imagine now that you’re actually living together. He taken you out on a proper date yet?”

He could feel his cheeks heating up, but he caved and answered honestly. “Three days ago.”

Benny allowed himself a satisfied smile before he became serious again. “So what, you’re so ashamed to be dating him that you can’t even bring yourself to admit it to me?”

“It's not like that,” he sighed. “I’m just not entirely sure what’s even going on, so I’m not talking about it.”

“Maybe you should talk to him about it.”

“Maybe you should change the subject,” he countered pointedly.

Benny accepted defeat, and the rest of the afternoon passed more comfortably. Dean really should have foreseen how that would change when Crowley got home. Maybe he should have made an effort to ensure that Benny was gone by then, but it wasn’t like he was doing anything _wrong._ He was hanging out with a friend, there was no reason to hide that – aside from the fact that he was pretty sure that Crowley at least suspected that they used to sleep together.

Dean and Benny were sitting in the living room watching Doctor Sexy (well, Dean was watching it, Benny was making fun of it), when the sound of the front door opening was immediately followed by Crowley's voice, “Dean, whose car  is-” He stopped talking as he turned into the living room to see Dean and Benny lounging on the couch.

Dean looked back at him with an easy grin. “Hey, you remember-”

“Benny, right?” he interrupted coolly, his gaze as it landed on Benny non-too-friendly.

“Yeah.” Benny's answering smile was pleasant, but his eyes were cautious. “You've got a nice place here.”

“I do. Nice things, too.” He pointedly didn’t break eye-contact as he reached over the back of the couch to run his hands through Dean's hair.

Benny’s smile slipped slightly, his gaze becoming colder to match Crowley's. “I didn’t realize Dean was a _thing.”_

Anger flickered in Crowley's eyes, and Dean quickly jumped to his feet, cutting him off before he could respond. “Okay, cool it, both of you. Benny, he didn’t mean it like that.” He turned around to face Crowley, capturing his gaze. “Can we talk? Alone?”

“Of course,” he said smoothly. “I’m not the reason we’re _not_ alone.”

He sighed and stalked out to the entry way, closing the doors to the living room once Crowley had joined him.

“Okay, not that you aren’t hot when you get all jealous, but what the hell?” he demanded as he rounded on him.

Crowley glared at him. “You used to sleep with him. Excuse me if I don’t like to see you two cozying up together on _my_ couch.”

“He’s my _friend,_ Crowley. You don’t see me throwing a hissy fit over you still being friends with Gabriel.”

“I don’t invite Gabriel over to the house.”

“Well, I wouldn’t care if you did. I don’t feel threatened by him.”

“Well, I certainly don’t feel threatened by _him,”_ he spat, nodding toward the door.

Dean crossed his arms over his chest. “Then I don’t see what the problem is. Benny and I are just friends, so if you don’t feel threatened by that…”

“Of course I don't!”

His retort was cut off as the door opened and Benny stepped out into the entryway. “I think I should probably be going,” he said, his eyes flickering between Crowley and Dean before resting on the latter. “It was nice catchin’ up, brother.”

“Yeah,” Dean sighed, a note of irritation still in his voice. “It was.”

“You’re more than welcome to stay for dinner,” Crowley piped up, prompting the other men to turn to him in surprise.

“I don’t want to intrude,” Benny said cautiously.

“Nonsense,” he dismissed, his smile not quite genuine, but not cold, either. “Dean’s the one who does all the cooking, anyway. It’s no inconvenience to me, whatsoever.”

“I suppose I can stick around, then…” He glanced at Dean, but he was still staring at Crowley, trying to figure out what he was playing at.

“Excellent,” Crowley said as he turned to Dean, ignoring the confusion on his face. “What’s for dinner?”

“Uh… what do you two want?” he asked, tearing his eyes away from Crowley to look between them both.

“What’ve you got?” Benny asked.

“Just about anything you could want,” he chuckled. “And then some.”

“How about burgers? Make it easy for you.”

Dean shrugged. “Works for me. Crowley?”

“I’ll make due,” he answered, resigned. Dean had often teased Crowley about burgers being too simple for his fancy-ass tastebuds, but he had admitted that Dean's burgers were better than most.

“Alrighty, then. I’ll get that started.”

“I’ll join you both in a minute – I’m going to take care of Juliet.” He leaned in close to Dean as he walked past him to mutter, “See? Not threatened.”

Dean rolled his eyes. He should have known. Of course Crowley was doing all this to prove a point. And _that_ had always worked out so well for them in the past.

Surprisingly, dinner went smoothly, though. Sure, Crowley touched and kissed Dean every chance he got to stake his claim, but he still made an effort to be friendly. He even became more genuine as the evening wore on as he realized that he actually got along with Benny fairly well.

“So, Benny, what do you do?” he asked after they had all finished eating and they were just relaxing at the table.

“Nothing right now,” Benny answered without quite looking at either of them. “It's hard to find work when you’re out in parole. Hard to do anything, really.”

Dean frowned. “What? How are you getting by?”

“I find work where I can.” He shrugged nonchalantly. “Gets me enough to survive.”

“I’m surprised,” Crowley said. “What, given your past and how you used to make your living.”

“It's hard not to fall back on old habits,” he admitted. “But whenever I’m tempted, I just remind myself that this idiot-” He pointed to Dean. “-stuck his neck out to get me out on parole, and I can’t let him down, now can I?”

He smiled, his eyes sliding to the side to glance at Dean, his gaze surprisingly soft. “Funny, the effect he has on people, isn't it?” he asked, returning his attention to Benny.

“Indeed,” he agreed with a grin.

Dean cleared his throat, hoping that he wasn’t blushing as much as he feared he was. “You should have told me you were struggling,” he said to Benny, steering the conversation back on track.

Benny shook his head. “You have enough on your plate.”

Crowley's expression was thoughtful. “I'm curious, what do you _want_ to be doing?”

“Ideally? I’d like to be a chef. But I blew my shot of doing anything more than flippin’ burgers a long time ago.”

Dean started to turn to Crowley, but he was already speaking. “Maybe. Maybe not. Were you aware that the Glasshouse is in need of a new chef?”

He scoffed. “If Biggerson's won’t hire me, the Glasshouse certainly won't.”

“I wouldn’t be so sure. In fact, I can _guarantee_ that you get the job – assuming you’re any good.”

Benny hesitated “Appreciate it, but I’m goin’ to have to turn you down. I’ve made enough bad decisions in my lifetime – I’m not getting involved in anything else.”

“That’s not what I’m suggesting,” Crowley assured. “I’m merely offering a favor to a friend of Dean's.”

He still looked skeptical, so Dean spoke up. “He’s true to his word. And if he tries to pull anything, I’ll put a stop to it.”

“I don’t doubt that,” Crowley chuckled. “So, what do you say? Interested?”

“Don't know how I couldn’t be,” Benny admitted, a grin curling up the corners of his mouth.

“Then, how about you come over and cook for us sometime? If I’m impressed, the job's all yours.”

He nodded. “I can’t thank you enough.”

“Oh, don't worry,” Dean said with a smirk. “I’ll thank him plenty for you tonight.”

Benny chuckled. “I’m sure you will.”

Well, now there were at least two relationships in his life that Dean didn’t have to keep separate. It still hurt having Sam apart from everything else that was going on with him, but it was something.


	11. Complications

“Rise and shine, darling,” Crowley's voice broke the still silence of the morning. “We have a busy day ahead of us.”

Dean groaned, pulling the blanket over his face. “Then you shouldn't’ve kept me up,” he grumbled.

“Didn’t hear you complaining last night.” He grabbed hold of the blanket, yanking it off of him. “Come on, eat your breakfast.” He set a tray laden with pancakes and orange juice down on the bed beside him. Dean blinked at it before his gaze moved up to Crowley, his eyes narrowing.

“You made breakfast?” he asked suspiciously as he pushed himself into a sitting position.

“Obviously.”

“What do you want?” he demanded flatly.

Crowley’s eyes widened innocently. “I can’t make you breakfast without wanting something?”

Dean raised his eyebrows at him, waiting expectantly.

He sighed in defeat. “You know how I said that you’d have today off?”

“Seriously? The next meeting is tomorrow, I got all the information, what could I possibly have to do?”

“I was thinking…” He picked up the tray again, passing it to Dean so that he could sit down beside him. “There’s really no point in presenting the information to the rest of the team before bringing it to Abaddon.”

Dean choked on the bite of pancake he had taken. “Let me get this straight,” he said once his airways were clear. “You want the first person I try to blackmail for you to be one of the toughest you’ve gone up against?”

“You won’t be alone,” he assured him.

His eyebrows furrowed. “Don’t you have work at the prison today?”

“I _did_ , but I’m terribly ill, you see.”

Dean rolled his eyes. “Nice.”

“My business comes first,” he said with a shrug.

Of that Dean was well aware. Crowley's business would always come before everything else in his life, and he couldn’t expect anything else. Not that he minded. He didn’t need anything else.

“And this was, I get to spend the day with you,” Crowley added.

“A pretty nice bonus,” he teased.

“Indeed,” he agreed, the gleam in his eyes that appeared whenever he boasted about Dean.

Dean shook his head slightly, brushing it off as he took another bite of his pancakes.

Crowley sighed. “Why do you insist on downplaying your worth?”

“I didn’t say anything!” he protested through a mouthful.

“You were thinking it.”

He couldn’t deny that.

“Do I need to call Benny to back me up?” he demanded.

At that, he had to laugh. “Bet you never thought you’d be saying that.”

“Definitely not. But… he’s not so bad,” Crowley admitted, slightly reluctantly.

“Told you.”

“Yes, yes, I know. So… you don’t miss sleeping with him?” he asked nonchalantly.

Dean looked at him in mild disbelief. How the hell was he supposed to answer that? He shook his head slightly, choosing his words carefully. “I mean, it was nice sleeping with him, but I’m not going to run off with him over it. I haven’t even slept with him since before we started sleeping together.”

He raised an eyebrow in interest. “Really?”

“Really. He _somehow_ got the idea that you could be possessive, and he didn’t want to risk it – no idea where that came from.” He winked. “Really, though, we discussed at the beginning that neither of us wanted a relationship, and even after you and I hooked up, I checked with him, and he was cool with it. You have nothing to worry about there.”

Crowley was silent for a couple of beats, not quite looking at him. “Well… good,” he finally said, but his voice seemed a little stiff.

Dean frowned. “You sure?”

“Of course. If you two are truly not interested in relationships...”

“Nope. He’s just a friend that I enjoyed sleeping with – past tense.”

“Right…” He nodded slowly. “So, nothing has changed?”

“No…” he said, confused. Hadn’t he made it pretty clear that he didn’t have any desire to run off with Benny? Well, maybe he was worried that that might be what Benny wanted. “I think he knew that I… had a thing for you, before I did,” he muttered, slightly reluctantly. “He’s teased me about you a lot… you know, in a supportive way.”

“How cute,” he mocked, but Dean could tell that his heart wasn’t in it.

“Hey,” Dean said firmly, capturing his gaze. “Even of he did want more – which I _know_ he doesn't – that’s his problem.”

“I’m glad to hear it,” he said briskly, the way he always did when he was ready to move on to a new topic of conversation. “But perhaps we should turn our attention to the task ahead of us.”

It still seemed to Dean that there was something… off, but if Crowley wanted to brush it off, then he could, too.

Then again, maybe it would have been better to press it more, maybe that would have delayed their phone call with Abaddon, which went just _swimmingly._

“So, what now?” Dean demanded as he slumped back into the desk chair.

“We don’t have a choice,” Crowley said calmly. “We turn in the evidence we have against her.”

He froze for a moment, before shaking his head slightly as he turned to face him. “I promised Cain I wouldn’t take this to the cops.”

“You…” He sighed in frustration. Dean knew how strongly Crowley felt about keeping his word, and so there was no way that he’d ask him to break his. Whatever else you could say about Crowley, he was a man of integrity, and he was certainly not a hypocrite. After a couple seconds, he met his gaze, resolve in his eyes. “You won't. But I made no such promise.”

“Crowley-” He started to protest, but Crowley cut him off.

“If we don’t follow through, it could mean the end for all of this.”

“You didn’t follow through with Dick Roman,” he pointed out.

“Only because just as I was closing in, you killed him. So. Unless you want to kill Abaddon, we're out of options.”

Dean’s shoulders slumped in defeat. “You’re _sure_ there’s no way to keep Cain out of this?”

“I’m sorry.”

“Dammit,” he muttered.

“Cain’s just as guilty as she is,” Crowley said placating.

“Yeah, but he walked away. He deserves to be able to live his life in peace.”

“Of course he does. But I’ve found that people very rarely get what they deserve.”

*

Naturally, the rest of the organization was quick to point out that the fact that they had to now take action against Abaddon meant that Dean had failed at his job. Even after Crowley assured them all that Dean's information had been perfectly adequate and that there would always be people out there who just wouldn’t cave to blackmail, they wouldn’t hear it.

“It appears that the majority of us are in agreement,” Marsha declared. “This was a failed experiment – _Dean_ isn't cut out for his role.”

Crowley had had enough. “What do you think this is? A democracy?” he demanded angrily, effectively silencing the room. “Let me make it very clear, _I’m_ in charge here. You don’t get to make demands of me. You have nothing to stand on. What are you going to do? Quit? Assuming you like your husband having his fancy job to make you feel like you aren’t the nobody that you are, I _wouldn’t_ recommend it.” He paused, glowering at her, giving his words a chance to sink in. “The only person here whose opinion holds any weight is Dean. The rest of you can keep your mouths shut unless you have any _relevant_ information to share.”

Marsha looked indignant, but she did the smart thing and stayed quiet. Dean glanced over the rest of the table to see that everyone’s expressions were varying shades of angry or frightened. The only exception was Gunner, who had been studying Dean and Crowley all meeting and now looked faintly amused. Dean was pretty sure that even he looked a little startled.

“Now that that’s cleared up,” Crowley continued. “Meeting adjourned.”

“But what about-” Carl started, but was silenced as Crowley turned his glare on him.

“Did I stutter?”

Everyone left considerably quicker than had done after the previous meeting. Within a minute, Dean and Crowley were the only ones left in the dining room. Crowley sighed, dropping his head to his hand.

“Thanks for that,” Dean muttered, a little unsure of how to act after that display.

He shrugged. “They needed to hear it.” He rubbed his fingers in a circle against the side of his forehead. “I wish I had taken off today instead of yesterday.”

Dean frowned. “You have to go into the prison?”

“No, I meant this.” He waved his hand around the empty room.

The corner of his lips quirked up slightly. “Sorry, babe. A little hard to take the day off when you run the company.”

Crowley looked over at him. “You know, when I started this business, it was all about power – getting as much money, controlling as many people as I could. When did it turn into listening to a bunch of morons complain and trying to solve all their problems?”

“I’m gonna hazard a guess and say when you started to hire people.”

“It’s sad how true that is,” he sighed.

“Sounds like you need a vacation,” Dean suggested, half-hoping that he would agree and they’d get to go on a vacation together.

Instead, he scoffed. “I don’t have time to go on vacation.”

“You’re the boss, you could make time.”

“If only,” he sighed as he rose to his feet. “Come on, we need to send some incriminating evidence into the police, and then make about 50 other calls before anyone starts to think we’re loosening our grip.”

As Dean stood up and followed after him, he tried to convince himself that getting Abaddon arrested was a good thing. And it was, really, but at the price of putting an at-least-now-innocent man in prison? Dean had been there, and now he was about to be the reason that Cain was. His first job for Crowley was turning out just great.


	12. Something Unexpected

Dean was glad to see that his first job for Crowley hadn’t been setting the tone for how all of his jobs would go. Just the opposite, in fact. Everyone that Dean approached since Abaddon had folded, finally earning him the respect of the majority of the organization. Even Marsha hadn’t been able to find anything negative to say about him in their past couple of meetings. All in all, Dean was feeling pretty good about himself – at least, when he didn’t think about what exactly he was doing and the rift that was growing wider between himself and his only remaining family every day. He could barely have a conversation with Sam anymore, and he had taken to ignoring all of Bobby’s calls.

On the bright side, Benny had become a bigger part of his life once again. Crowley had gotten him the job at the Glasshouse, and he often came over whenever he got off work. Dean had been a little worried that, even with how much Crowley had warmed up to Benny, he wouldn’t be all that comfortable with it being just him and Dean while he was at work. He didn’t seem to mind, though. It seemed that, even though Crowley often boasted of the fact that he didn’t trust anybody, he did actually trust Dean to some degree. This, though – _this –_ he had not seen coming.

Dean was laying on the couch, his hands behind his head and his feet propped up on Benny’s lap. “When’s your boyfriend coming home?” Benny asked casually.

Dean rolled his eyes. “Still not my boyfriend,” he muttered, a note of exasperation in his voice.

“And whose fault is that?”

“Whose fault is what?” Crowley’s voice came from around the corner, and a second later, he entered the room.

“Whose fault is it that I have a headache,” Dean hurried to say before Benny could do more than open his mouth, looking up at Crowley over the back of the couch. “And it’s yours.”

“Mine?” He arched an eyebrow, leaning back against the door frame. “And how exactly is that my fault?”

“Oh, I don’t know. Maybe because you never shut up,” he shot at him, the faint smirk on his lips contrasting his irritated tone. “I had to listen to you talk all day yesterday, and I’m still suffering the effects.”

His eyes narrowed. “Oh, so perhaps I’ll just leave you to run the next meeting on your own, shall I? If my talking bothers you so much.”

“Fine by me. I’d probably do a better job than you do, anyway.”

Benny chuckled. “Maybe I should take my leave before you two start ripping each other’s clothes off.”

“We’re not-” Dean started, but Crowley cut him off.

“Why? Think the both of us would be too much for you?” he challenged.

Benny’s eyebrows shot up. “You’re asking if I can handle you both?”

Crowley’s eyes sparkled as a smirk curled up his lips. “Mmhm.”

Dean blinked at him in surprise as he realized that he might _not_ be merely teasing in his usual Crowley way. He might actually be insinuating that he _wanted…_ “Crowley…”

There was a speculative gleam in Benny’s eyes as he crossed his arms over his chest and leaned back against the arm of the couch to keep both Dean and Crowley in his line of sight. “Well, if that’s the question, I most definitely can.”

“You sound awfully confident.” He pushed himself off the doorframe, taking a few steps into the room. “Care to prove it?”

Dean’s mouth dropped open, but he hardly noticed. He was too busy staring at Crowley. He was seriously suggesting a _threesome_ with _Benny._ Benny, who a month ago he hadn’t wanted anywhere near Dean.

“Love to,” Dean was pulled from his thoughts as Benny spoke. “I think Dean should probably have a say in this, though.”

“Oh, of course.” Crowley turned to him with a grin. “What do you say, darling?”

Dean’s mind was so busy spinning that it took him a minute to remember how to speak. “You’re serious?” he asked slowly.

He held his hands out, palms up. “Do you want me to be?”

He considered it for a moment. Considered being in bed with both Crowley _and_ Benny. Considered their lips on him. Their hands. Considered them trading off fucking him. Considered Benny’s cock in his ass as Crowley thrust down his throat…

He swallowed hard. “Y-Yeah. I do.”

“Well, then.” His eyes flickered to Benny, whose hand began to slide up Dean’s leg. “I do hope you can play by my rules.”

“I’ll try my best,” Benny drawled, his hand not ceasing its progress. “Never been big on rules, though.”

“I think you’ll find that the right incentive can go a long way as far as following rules is concerned.”

His eyes drifted back to Dean. “You might have a point there.” He leaned in and, before Dean could do more than catch his breath, he grabbed the front of his shirt and pulled him into a kiss. Benny’s lips were eager and demanding as he kissed him, as if… well, as if they hadn’t done anything in months. Some part of Dean wondered if Benny had gotten any action since him, but he couldn’t devote much thought to the matter, as Crowley sidled onto the couch behind him, grabbing him by the waist and pulling him back against him, taking Benny along for the ride so that Dean was sandwiched between the two of them.

Damn. Dean could already tell this was going to be one hell of a night.

* * *

 

Dean groaned as he opened his eyes. He might have run the risk of thinking that last night had just been a really awesome dream if it weren’t for how fucking sore he was. Then there was also the fact that when he rolled over, Benny was looking at him with an easy grin. “Mornin’”

“Morning…” he muttered, slightly awkwardly as he pushed himself up and glanced around the room, but it quickly became clear that the two of them were alone. He wasn’t sure if that made things better or worse. Of course, last night had been amazing, he just… wasn’t exactly sure how it had happened and what it meant. Was it just something fun that Crowley had wanted to try, or did it mean that he no longer wanted to be exclusive? Or what if he didn’t want to be anything, anymore? Dean had thought that his friendship with Benny no longer bothered him, but what if last night had been some sort of twisted test to see if he’d still sleep with him?

“Dean? Somethin’ wrong?”

He shook his head slightly, not necessarily in answer, more to push his thoughts away. “Do you know where Crowley is?” he asked, trying to not let his worry creep into his voice.

“Can’t say I do,” he said with a shrug. “Only woke up a few minutes ago, and he was already gone. I take it that’s not normal?”

“Only if he can’t stay,” he sighed.

“How sweet.”

Dean’s eyes drifted to the side and he caught sight of a piece of paper on the nightstand. He quickly snatched it up and read the familiar handwriting, _‘Sorry, darling, Satan called me in for work. Hope you enjoyed last night as much as I did – or even more, as I’m sure that’s more accurate. I’ll be home for dinner. xo’_ He smiled to himself as he finished, lowering the note down to his lap.

“So, what’s the love note say?” Benny teased.

Dean rolled his eyes. “He got called into work. He’ll be home for dinner.”

“And you’re not a couple?”

“No. We’re not. We’re just…” But Dean still didn’t know what exactly he and Crowley were to each other.

“Dating exclusively?” he volunteered with a wry smile.

“Look, does there have to be some kind of label? Why can’t we just _be?”_ He was content with that. Why did everyone have to label things? He and Crowley could go on dates, sleep together, live together… so what if he didn’t know what exactly that all meant? He should just enjoy the moment. It’s not like it bugged him or anything, not knowing. Things were just fine as they were.

“You’re right.” Benny held his hands up in surrender. “You don’t need to label it.” He paused, a speculative look in his eyes as he looked at Dean. “But have you at least told him that you love him?”

Dean blanched. “I – I don’t…” he stammered, but Benny looked unimpressed.

“Please, brother. It’s painfully obvious.”

“But, I don’t! I mean, I…” He sighed. “And even if I did, it’s not like I could do anything about it,” he muttered to his lap.

He arched an eyebrow at him. “Why not?”

“Why do you think?” he demanded. “It’s _Crowley._ He’d probably call off… whatever the hell this is if I told him that.” Maybe, if he was being perfectly honest with himself, his mind had started to wander as of late as he imagined what it’d be like to have more with Crowley – to have something he knew was real – but he knew it would never happen, and what he had with him now was better than nothing.

“Dean,” Benny sighed. “You’re my best friend, but you’re not always the brightest. You really think he doesn’t feel the same?”

He looked at him incredulously. “Come on, Benny, he’s not the kind of guy that falls in love.”

“Not the kind of guy who does exclusive relationships, either,” he pointed out.

“Says the guy I had sex with last night,” Dean threw back at him. “And yeah – threesome – it’s different – whatever. He’s clearly not entirely opposed to me being involved with someone else.”

“Wow. You really are an idiot.” He shook his head. “You know he took me aside last night and told me not to get any ideas because if I ever touched you without his permission, he’d skewer me?”

“He really said that?” he asked, the corners of his lips tugging up slightly. Wow, how screwed up was his and Crowley’s relationship that he found _that_ sweet?

“When someone threatens you, you tend to remember it.”

He soaked that in for another couple of seconds, then shook his head. “Alright fine, but that’s all possessiveness, not… not _love.”_ Saying the words was like ripping off a band aid he hadn’t known was there, and his face twisted slightly at the unexpecting sting. Shit. He really had gone and fallen in love with the worst possible person to fall in love with, hadn’t he?

Benny shook his head. “That possessiveness comes from somewhere. And I see the way he looks at you. He loves you.”

He quickly shoved down the hope that threatened to rear its head at those words. “Then why hasn’t he said anything?”

“Probably because his appearance is so important to him, he won’t say it first. Or maybe for the same reason you won’t.” He shrugged. “I’m not the expert on this. Ask him.”

Dean sighed, looking away. “Look, Benny. I know you’re trying to help, but Crowley just isn’t the kind of guy who-”

“Who what? Who goes out of his way to get a guy who’s shot him down numerous times? Who risks disrupting his entire operation to make him second-in-command? Who continues to bend over backwards for him every day?”

“He doesn’t-”

“He moved you in with him,” Benny interrupted again, “stopped seeing anyone else, gave your friend he didn’t even like a job, invited said friend to bed, spoils you every chance he gets – if that’s not bending over backwards, brother, I don’t know what is.”

He just looked at him, unsure how he was supposed to argue against that. Because Crowley _didn’t_ love him. There was no way. The idea would be laughable if it didn’t hurt so damn much. But those were the facts. Crowley just didn’t… well, he _didn’t_ do any of those things that Benny had listed. At least, Dean never would have thought he would. But he did. So, maybe…

He shook his head. Hope was a dangerous thing, and this was not the kind of thing that he needed to get his hopes up about.

“Dean,” Benny spoke after the silence had stretched on for a good minute. “It’s getting to the point where if you don’t tell him, I will.”

Dean glared at him for a second before he gave a small sigh of defeat. “Alright, fine, let’s say I’m listening to you… how do I tell him?”

He thought about it for a moment. “Romantic, candle-lit dinner? I know a pretty good chef who might be willing to do you a favor.”

He rolled his eyes. “I can cook our own dinner just fine, thank you very much.”

“Yes. But I can cook a better one. And this way I can make sure it happens.”

“Please tell me you’re joking,” he muttered hopefully.

He wasn’t.

Despite Dean’s many protests, when Crowley arrived home that evening, Benny led him to the dining room where Dean was sitting at the table. The room lit only by candlelight, which hopefully disguised the embarrassed flush on Dean’s cheeks.

Crowley looked curiously between the two of them. “What exactly is going on?”

“Have a seat,” Benny motioned to the seat caddy-corner from Dean, where a place had been set for Crowley. “I’ve prepared smoked salmon for dinner with a side of creamed spinach and herb-roasted potatoes.”

“Sounds delicious,” Crowley said, though his eyes were narrowed in mild suspicion as he took his seat.

He smiled, unfazed. “I’ll let you two enjoy.” And with that, he backed out of the room, closing the door behind him.

He arched an eyebrow at the door for a moment, before turning to Dean. “Benny trying to say thank you for getting to sleep with you again?”

Dean very nearly said yes. It was a plausible explanation, after all, and would surely end a lot better than the truth. But instead, he sighed. “No… not exactly,” he muttered without quite looking at the other man. The thing was, as much as Dean didn’t want to do this, as much as he was sure that this was a horrible idea – Benny had had him thinking about these stupid feelings he had for Crowley all damn day, and he didn’t know how he was supposed to go on pretending that they weren’t there, anymore. And he knew that Benny had probably been counting on that.

Crowley’s other eyebrow rose to join the first. “Oh? So, what’s the occasion, then?”

“Um, I just…” He cleared his throat, his eyes darting to his face and then quickly away again. “I wanted to… to tell you something.”

In his peripheral vision, he saw Crowley’s expression become closed off, the way it always did when he was determined to keep his emotions out of the conversation. Instantly, all of the reasons that Dean knew this was a bad idea overpowered his new desire to get everything out in the open, to _know._ He found himself wishing more than anything that he could take his words back, that he could get out of this whole mess. Dammit. He had already lost his family because of how he felt for Crowley, and now he was about to lose him because of it, too.

“And what did you want to tell me?” he pressed evenly.

He took a deep breath. Well, there wasn’t really any way to turn back now. Unless he could think of something else to tell him that would be worth surprising him with a candle-lit dinner over…. Nope. Nothing. “Okay,” he braced himself, turning away from Crowley completely to stare at the wall across the table from himself. “Um… you know, things between us have really – really taken a turn I never expected. I mean, I hated you at first, and then we were sleeping together, and now we’re exclusive, and it’s just-”

“Dean,” Crowley interrupted him, his level façade cracking slightly. “If you planned a candle-lit dinner to soothe the blow of breaking up with me, you are the _worst-”_

“What?” Dean’s gaze snapped back to him in shock. “No! I’m not breaking up with you, I love you!”

He blinked in surprise as silence filled the room and Dean realized what he had just said. Well, that was that. It was out there now, and there was nothing he could do about it. 

“You what?” Crowley asked, his voice impassive.

He licked his lips nervously, but he didn’t turn away this time. The damage had already been done, after all. Now all he could do was see how it played out. “That’s what I wanted to tell you. I… I love you.”

“Oh…” His tone and expression were still unreadable, and Dean could feel his nerves being stretched tighter with every second of silence that ticked by. Finally, a very faint smile turned up the corners of Crowley’s lips. “I love you, too, Dean.”


	13. Halloween

This was without a doubt the swankiest Halloween party that Dean had ever been to. Then again, it was Crowley’s party, so it wasn’t as though he had expected anything different.

Gunner chuckled as he walked up to Dean and Benny, his eyes running over their costumes. “You two coordinate?”

Dean sighed. “No. The vampires in Van Helsing don’t even look like that,” he pointed out for what felt like the tenth time that night, waving his hand at Benny.

He shrugged. “Still works.”

“Certainly better than wearin’ your work clothes,” Benny said, his voice slightly muffled because of his fangs.

“I don’t do costumes outside the ring.” He looked over at Bella as she called him over. “Excuse me.”

“Isn’t he cool?” Dean asked with a grin, once Gunner had walked away.

Benny rolled his eyes. “Remind me why I agreed to come to this.”

“Because you had nothing better to do on Halloween. And you’re a good friend who didn’t want to make me do this alone.”

“You’re not alone.” He nodded towards Crowley, wearing a demon costume and ordering around someone with a tray of hor d’oeuvres.

“He’s hosting.”

“As his boyfriend, aren’t you technically co-host?”

“Keep your voice down,” he hissed. “No one’s supposed to know about us.”

Benny raised an eyebrow. “You seriously think you can keep it a secret?”

“It’s worked so far.”

“And no one’s picked up on it?” he asked skeptically.

“No!”

“That you know of.”

“Benny, no one has-”

“Dean,” he cut him off. “I hate to break it to you, brother, but you two are kind of obvious. I’d bet money that most people here at least suspect something’s up.”

“Well, as long as nothing’s _confirmed,_ we don’t have a problem, right? Right. So, drop it.” Dean shook his head as he turned away, scanning the crowd for the least painful person to socialize with.

It was about an hour later, when Dean was on his way back from the bathroom, that the doorbell rang. He frowned as he drew to a stop in the entryway. As far as he knew, everyone from their little organization was there, and there weren’t many others who knew the gate code. He glanced back towards the drawing room briefly, then moved to answer the door.

“Trick or treat!” a young boy with a bedsheet over his head said, holding out a plastic pumpkin pail.

Dean’s frown deepened. “How did you…?”

“Jack!” a familiar voice called as a figure dressed as an angel came up the steps. “I told you to wait for me.”

“Gabriel?” he asked incredulously, turning to the man.

“Oh, hey, Dean-o. Guess I should’ve expected to see you here.”

Dean’s expression became even more incredulous as his gaze returned to the bedsheet ghost. “You have a _son?”_

Gabriel laughed. “Oh, no. This is my nephew, Jack.” 

“Oh. Hey, Jack.” He smiled down at the boy for a moment, before he turned back to Gabriel, his smile faltering. “Wait. Which brother-?”

Before he could finish the question, Crowley’s voice rang out behind him. “Gabriel?” he asked curiously. “What are you doing here?”

“Just taking my nephew trick-or-treating,” he answered with a grin, though his eyes were cautious. “You do have candy, don’t you?”

Dean looked back at Crowley in time to see his eyes narrow. “A closed gate generally means trick-or-treaters not welcome,” he said coldly as his gaze slid down to Jack. “You’re lucky Juliet hasn’t taken your leg off. She doesn’t take kindly to unwelcome visitors.”

“Crowley!” Dean scolded. “He’s just a kid,” he added in an undertone when Crowley reached his side.

“And I don’t do kids,” he hissed in return. “Particularly not _Lucifer’s son.”_

Ice settled in Dean’s stomach. That was what he had been afraid of. Maybe Crowley wasn’t so out of line, after all…

Gabriel sighed. “Jack, why don’t you go wait in the car-”

“But-” the kid started to protest.

“I’ll be sure to get you some candy,” he assured him, patting him on the head. “Go on, now.”

Jack hesitated for a moment longer, then turned to go. “See if they have nougat!” he insisted before running back to the car.

“Gabriel, you cannot bring him here,” Crowley ground out as soon as the kid was out of earshot. “I know you like to play all sides in your family, but leave me out of it! I have Lucifer breathing down my neck enough as it is.”

“And how is giving a kid some candy going to make things worse for you?” Gabriel demanded. “It’s not like he’s compiling a report for his father.”

“So far as you know.”

He shook his head. “You’re paranoid.”

“Really? Who did the boy just see me with at _my house?_ What do you think Lucifer will do when he finds out that Dean was here?”

“Jack won’t tell him,” he insisted, a note of exasperation in his voice. “He doesn’t even know who Dean is.”

“You have no way of knowing-”

“Look, Crowls. I know you hate my brother – I’m not so fond of him, either – but you can’t put all of that hatred on Jack. He’s an innocent kid.”

“Gabe, Crowley’s right,” Dean spoke up with a sigh. “Any child of Lucifer’s ain’t innocent. Who knows what all thoughts he’s put in his head?” He shook his head. “Really, what were you thinking?”

“I was thinking that the kid deserved to have some _fun,”_ he snapped. “He’s not evil incarnate, no matter what you two choose to believe. So, if you refuse to listen, I suppose I’ll just take the candy and be on my way.” He held out a hand expectantly.

Crowley glared at him for a moment, before he stalked off into the other room, leaving Dean and Gabriel alone in the entryway.

“Dean-” Gabriel started imploringly.

“Save it,” he cut him off. “When I was growing up, I did everything I could to be just like my old man. His approval meant everything to me. And looking back, he wasn’t always in the right, but back then, I didn’t care – right to me was whatever my dad did.” He sighed, shaking his head slightly. “So, maybe the kid’s already evil, maybe he’s not – either way, he’s going to be following in his father’s footsteps, I guarantee it.”

He ground his teeth together, but before he could say anything, Crowley reappeared with a handful of candy that he shoved at Gabriel’s chest. “Take it and get the hell off my property,” he nearly growled.

“Gladly,” he said curtly as he grabbed the candy. Then he spun on his heels and stalked off, kicking the door shut behind him.

They both stood staring at the closed door in silence. Crowley was clearly seething, and while Dean certainly wasn’t happy, he was also very aware of the fact that Gabriel was Crowley’s closest friend, and there was probably some hurt fueling his anger. But Crowley wasn’t the kind of guy that was easy to comfort, so Dean was left feeling a bit at a loss.

“Think we’re in trouble?” he finally asked, his voice soft.

Crowley didn’t quite look at him as he turned away from the door. Yep, he was definitely hurting. But heaven forbid Crowley show a sign of weakness. “I hope not.”

“How bad do you think it would be?” he asked, leaning back against the wall. “If Jack told Lucifer. I mean, I know he wouldn’t like you associating with me, but it’s not like he can prove anything.”

“No. But he’ll start digging. And with his resources, it’s not a matter of if he’ll find something, it’s _when.”_

He dragged his hand down his face. “Guess we just gotta hope Jack doesn’t know who we are, then.”

“I _hate_ relying on hope,” he grumbled.

Dean gave a half-shrug, the corner of his lips turning up slightly. “Hey, it’s panned out for me, so far.”

* * *

 

Maybe hope really was worth something because when Crowley got home from work two days later, he reported that Lucifer hadn’t acted any differently towards him.

“He wasn’t particularly happy _or_ hostile towards me, and if Jack had said something to him, there definitely would have been some kind of sign,” Crowley leaned back in his chair, looking more relaxed than he had since Halloween. “I think it’s safe to say we’re in the clear.”

“Well, that’s a relief.” Dean sat down across the desk from Crowley, allowing himself a moment to bask in the release of the tension that he had been feeling for the past two days. He could only afford a moment, though, because Lucifer wasn’t the only reason they had both been so tense. “So… you talk to Gabriel today?” he asked hesitantly.

His expression grew darker. “No,” he said curtly.

He sighed. “Crowley, he’s your best friend.”

“I don’t have friends. And I don’t think you have any room to talk, as you’re the one avoiding your own family.”

His jaw dropped open slightly, unable to believe that Crowley had just thrown that in his face like that. “That’s different!” he snapped.

“Is it?” he challenged.

“I’m doing it for _you.”_

“Well, I didn’t ask you to make yourself miserable for my sake.” He glared at him pointedly. Dean knew it was Crowley’s way of saying he cared, but he still found it irritating.

“I’m not miserable,” he protested defensively.

Crowley arched an eyebrow at him. “That so? Tell me, Dean, your brother will be coming home for Thanksgiving break later this month, correct? And are you planning on seeing him?”

Dean looked away.

“That’s what I thought.”

“You know I can’t,” he muttered, still not looking at him.

“And you know you’ll never forgive yourself if you don’t,” he countered.

“There’s lots of things I’ll never forgive myself for.” He shrugged. “I’m used to it.”

He was saved from having to hear whatever Crowley’s retort was going to be by his phone ringing. “Sorry, gotta get this,” he said, pulling his phone out of his pocket and answering it without even looking at the caller ID. “Hello?” he answered, desperately hoping that he hadn’t just made a huge mistake and he hadn’t been rescued from one uncomfortable conversation by an even worse one.

“Hello, Dean.”

Dean blinked in surprise as he recognized the voice. “Cas?” He angled his body away from Crowley slightly as the other man’s eyes narrowed. “Hey, man. Long time, no talk. How’s it going?”

“I am concerned,” he said frankly, his voice grave. He had forgotten how odd Castiel could be sometimes.

“Alight… what’s up?”

“Did you strike a deal with Crowley MacLeod?”

The phone nearly slipped out of Dean’s hand. “Wh-What would make you think that?” His gaze snapped back to Crowley, whose eyebrows had furrowed at the change in Dean’s tone. After a moment’s hesitated, he put the phone on speaker, setting it down on the desk between them.

“I spoke to Gabriel today,” Castiel explained as Dean caught Crowley’s eyes over the phone, seeing his own worry reflected in them. “I never understood his friendship with Crowley, but they seemed hostile towards each other today, so I decided to ask him about it. He said that he had taken our nephew trick-or-treating to Crowley’s house on Halloween, and that Crowley had gotten upset because Jack had seen someone there that he would rather Lucifer not find out about. I can only assume he meant you.”

A sense of dread filled him. Of _course_ Castiel’s mind would immediately go there. Why had he never thought to consider that Castiel was probably the person most likely to suspect that something was going on between himself and Crowley? “Why the hell would it be me?” he demanded, doing his best to sound incredulous.

“I’m not blind, Dean. The interest he took in you was quite obvious. As was the interest you took in him.”

 _“What?_ I’m not interested in him!” he protested, noticing that Crowley’s expression, while still mostly worried, had also taken on a slight edge of amusement.

“Please do not act as though I am an idiot, Dean,” he said tiredly. “I walked in on you two about to kiss.”

“I… _fine,”_ he snapped. There was the chance that if he told a partial truth, he’d be more believable. “But just because a guy’s hot, doesn’t mean I’m about to sell my soul to him. Crowley’s a dick.”

“So, how _did_ that evidence on Dick Roman surface?” he demanded.

“I… I don’t know. It was an anonymous tip, wasn’t it?”

“Yes, it was. But it would have had to come from someone with considerable resources. I only know of a couple of people who could have pulled it off, and I don’t see Lucifer doing you any favors.”

He sighed. “Look, I wanted out of prison,” he said reasonably. “But not enough to make a deal with Crowley to get out. Promise.” And it was the truth.

“So, what else did he offer you?” he pressed. “Money for your family? A full ride to Stanford for Sam?”

Crap. Castiel knew him better than he thought he did. There was only one card left he could play. “Wow, Cas.” He shook his head. “You haven’t spoken to me since I got out of prison, and now you call me just to throw accusations at me and question everything I say? I thought you were my friend.”

“I thought so, too,” he said solemnly. “But I highly doubted that you would want to speak with me, considering that you won’t even talk to your own family.”

Dean’s gaze snapped down to the phone, his eyebrows furrowed in confusion. “How do you…? Sam,” he realized, feeling suddenly cold. “You’re still talking to Sam.” He had never imagined that Castiel would stay in contact with his brother once he had gotten out of prison, and for some reason, it didn’t sit well with him. It was just the thought of Sam complaining to Castiel about his brother who rarely answered his calls, and when he did, always got off the phone as soon as possible – the idea of Castiel comforting him, when Dean should be the one doing that. But he couldn’t because he was the cause of Sam’s pain. But wouldn’t actually talking to him – filling a conversation with lies, or even worse, the truth – just make it even worse?

“Well, he needs somebody to talk to, since he doesn’t have you,” Castiel said bluntly.

Well, didn’t that just feel like a slap to the face. He swallowed thickly, unable to find words to say to that. He glanced up at Crowley who looked furious – he was clearly barely holding himself back from saying something.

“I don’t know what you got yourself into, Dean,” Castiel continued. “But it’s not worth abandoning your family over.”

“I don’t think someone with a family as dysfunctional as yours should be giving family advice.” The words came pouring out of Dean’s mouth without any real emotion behind them. “You think you know what’s going on, but you don’t. And I don’t owe you an explanation, but if it will get you to shut up – I have trouble talking to my family because of the person I became in prison, _not_ because of Crowley. And I was with Benny on Halloween, for the record. Now, I’m done being interrogated. Don’t call me again.”

“Dean-”

He hung up the phone before Castiel could get anything else out, then he slumped back in his seat, closing his eyes as though that would block out everything that had just happened. But he just couldn’t get the image out of his mind of Sam calling Castiel whenever his own brother refused to talk to him.

“Dean…” Crowley said softly.

“I’m taking off for Sam’s Thanksgiving break,” he muttered without opening his eyes.

There was a moment’s pause. “I think that’s wise.”


	14. Family Reunion

Sam had sounded depressingly shocked when Dean had offered to pick up from the airport, but there had also been a definite note of happiness in his voice, so that was something, at least. And though Dean had been debating ever since that phone call whether it had been a good idea, when he got to the airport, he was glad he had decided to do it. Sure, he had never felt so much anxiety waiting for his brother before, but as soon as he saw him, he realized just how much he had been missing him. So what if things were awkward? He needed to be with his family.

“Damn, it’s good to see you, Sammy,” he said as he pulled back from the hug.

“You too, Dean,” Sam said with a grin. “Thanks for picking me up.”

“Course.” He picked up one of Sam’s bags and led the way out to the car.

“So, am I going to get to see your new place?” Sam asked a few minutes later as Dean pulled out of the parking space.

“Oh, it’s nothing special,” he said dismissively. “And you know me, it’s a mess. I don’t need you critiquing my lifestyle.” He threw him a grin before quickly changing the subject. “So, how are those California girls?”

For a second, it looked as though he wasn’t going to let the subject change slide, but then he rolled his eyes. “They’re alright, I guess.”

“You guess? C’mon! Tell me you’ve had at least one wild hookup since going off to college.”

“I’m not you, Dean.”

“Yeah, but you can still get laid – you’re not _that_ unattractive and dull. Hey, if it helps, you can always try to channel me.” He winked.

“Thanks, I’m good,” Sam retorted, the sarcasm palpable in his voice.

“Your loss,” he said with a shrug.

He shook his head exasperatedly. “So. Job still treating you well?”

“Oh, yeah. It’s great. My boss even gave me the whole week off to spend with you.”

His eyebrows shot up. “Seriously? I didn’t realize the shop was big enough to do that.”

“Well, it is.” Dean tried to think up some kind of detail he could give him, and he smiled when he got an idea. “And you’ll _never guess_ who brings his car there.”

“Who?”

“Gunner freakin’ Lawless!”

_“What?”_

“Yep. We’re on a first-name basis,” he said proudly.

“You mean when he reads your name tag?”

“Okay, first off, I don’t have a name tag. And second, I mean on a _date.”_

“You went on a date with Gunner Lawless?” Sam asked, every syllable ringing with disbelief.

“Oh yeah. Highlight of my year right there.”

“Wow. So, are you going out again, or…?”

“Nah. I mean, it was great, but…” He shrugged. “Something I can cross off my bucket list.”

“Of course.” He rolled his eyes. “I don’t get your aversion to relationships.”

“I don’t have a-”

“Yes, you do, Dean,” he said tiredly. “You avoid them at all costs.”

“Well, maybe I’m waiting for the right person,” he muttered, keeping his eyes trained on the road.

Sam hesitated, clearly having noticed the change in his tone. “Dean? Is there something you want to tell me?”

“No, course not.” His eyes flickered to Sam’s curious face then quickly away again. “So, your first night back home. What do you wanna do?”

They ended up going to a bar that Dean knew he’d be able to sneak his minor brother into – mostly because the bartender there knew not to cross him, but Sam didn’t need to know the details.

“This seems a little nicer than your usual scene,” Sam commented after they’d gotten their drinks.

He shrugged. “Some guys from work like this place. Guess it caught on.”

Dean looked over to the door as it opened – a force of habit he wasn’t sure when he had developed – and smiled as he recognized the man walking in. “Benny!” He waved him over automatically, then internally cringed. So much for avoiding conflict.

Sam noticeably stiffened as he turned to seize up the new arrival.

“Hey, Dean,” Benny greeted him as he reached their table. He turned to Sam and held out his hand. “You must be Sam. I’ve heard a lot about you.”

“Likewise,” he replied coolly without taking the offered hand. “You’re the guy from prison, right?”

Dean sighed. “Sam, this is my best friend, Benny,” he said pointedly. Sam hadn’t even been in town a day and they were already going to have a fight, weren’t they?

“And here I was thinking that this was too nice of a place for felons,” Sam said as if he hadn’t heard him. “Can’t imagine that someone out on parole would be able to afford being a regular in a place like this.”

Benny grinned bitterly. “As a matter of fact, I am a regular here. And no, I’m not stealin’.”

“Yeah?” he challenged doubtfully, blatantly ignoring the way Dean was glaring daggers at him. “What do you do, then?”

“I’m the head chef at the Glasshouse.” He inclined his head in a nod. “And yes, it pays as well as you think it does.”

Sam scoffed. “How did you manage to get a job there?”

“Good connections,” he said simply. His eyes flickered briefly to Dean, then back again. “I suppose I’ll let you two get back to it. Always good to see you, Dean.” He nodded to him, then turned and walked away.

Dean shook his head, his eyes shining with furious disbelief. “Seriously, Sam?” he said heatedly the moment Benny was out of earshot. “You know, you can’t complain about me not talking to you or not wanting to share things with you when you act like this.”

Sam looked at him in disbelief. “What’s that supposed to mean?” he demanded, taking on the defensive tone he had so often taken with their father.

“It means you say that you don’t care that prison’s changed me, it doesn’t make a difference, yadda yadda. But when you’re confronted with _evidence_ of that change, you end up treating my best friend like garbage!” He turned away from his brother, glaring at the wall instead.

“What do you want from me, Dean? I’m not gonna make nice with a guy from prison-”

“I’m a guy from prison, Sam!” he nearly shouted, his gaze snapping back to him. “And don’t go saying that I’m different, because that’s what I’ve been trying to tell you this whole time – I’m not. I had to make compromises in that place to survive, and now _am_ a different person – even worse than Benny, I promise you that. And if you can’t accept that, then maybe I made a mistake taking this week off.”

Silence fell between them, tense and uncomfortable. It had probably only lasted for a couple seconds, but it felt more like a couple minutes to Dean, and he couldn’t take it anymore. He got up and stormed out the door. Sam didn’t try to stop him.

“I ruined it, didn’t I?”

Dean had been so busy seething that he hadn’t noticed Benny standing by the road, more than likely waiting for a cab. He shook his head. “No, you didn’t. He did.”

“Hey, I don’t care if he doesn’t like me-”

“Well, I do,” he cut him off. “You’re the least complicated part of my life, and if I can’t even share that with him, what am I doing?”

“You’re spending time with your brother – probably the most important person in your life.”

He shook his head with a sigh. “I wish it was that simple, but… it’s like we don’t even know each other anymore.”

“So, let’s change that,” a voice rang out behind him.

Dean turned to see Sam walking out of the bar, his expression a mixture of sadness and hopefulness.

“Dean, I want you to be honest with me, not to feel like you have to hide a part of your life from me.”

“Well, you’re not making it very easy,” Dean said, crossing his arms over his chest.

He looked down. “I know,” he muttered before tentatively looking back up at his brother. “And I’m sorry. Anything you want to say… I won’t judge you for it. Promise.”

He nodded slowly. It was a nice sentiment, but Sam had no idea the kinds of things he was involved in now. He could promise not to all he wanted, he wouldn’t be able to help judging him if he knew the truth. And Dean couldn’t blame him – hell, he judged himself for it every day.

“Thanks, Sam,” he muttered, not quite looking at him. “But there’s not really a lot to say. It’s all internal, you know. I just feel… different.”

Sam nodded. “I get it.” He glanced over to where Benny stood awkwardly to the side. “I’m, uh… I’m sorry about before. You want to… join us for drinks?”

Dean looked at his brother in surprise before his gaze shot back to Benny, who was regarding Sam with an eyebrow raised curiously.

“Maybe another time,” he said slightly hesitantly. “But thanks, anyway.” He inclined his head towards him, then turned and took off down the street, clearly deciding to try to catch a cab in a place with a little less tension.

“So…” Sam started once Benny was a decent distance away. “You want to go back in? Or are you just gonna drop me off at Bobby’s?”

Dean hesitated for a moment, then he sighed. “Let’s go back in.”

* * *

 

Dean didn’t go inside when he dropped Sam off at Bobby’s later that night. He didn’t need to have the same fight twice in one day. The next day, though, he had promised Sam that he would pick him up and they could go see a movie at the old theatre they used to always go to as kids. And he knew that he wouldn’t be able to get away with just waiting in the driveway until Sam came out.

He took a deep breath as he walked up to Bobby’s front door. He wondered for a second if he should knock, but that would be acknowledging the distance that had formed between him and his basically-uncle, and he would rather not do that, if he could avoid it. So, he pulled open the front door and walked inside the way he had since he was a kid.

“Sam?” he called as he stepped inside. “Bobby?”

“In here, Dean,” Sam called from the drawing room.

Of course it wasn’t going to be as simple as grabbing Sam and running. He reluctantly turned into the drawing room to see Bobby standing up from his desk and Sam standing by the window with… Castiel.

“What the hell is this?” he demanded, looking between the three of them. No one had said anything yet, but it sure looked like an intervention.

“We need to talk, boy,” Bobby said firmly, walking around his desk to stand beside Sam, creating a united front against Dean.

He shook his head slightly as he caught his brother’s gaze imploringly. “Sam, what the hell?” He had thought that they had made progress the night before. Sure, he was still lying to him, but Sam didn’t know that. Or at least, Dean had thought he didn’t.

Sam took a deep breath. “Cas came by this morning…”

“Of course he did.” His gaze snapped to the right to glare at the guard.

“Dean, I am only trying to help,” Castiel said in what was probably meant to be a soothing voice.

“Well, you’re not,” he snapped.

“Dean,” Sam raised his voice slightly, cutting him off before he could yell at the other man. “What kind of a deal did you strike with Crowley?”

Dean huffed a humorless laugh. “You seriously believe that-”

“I know it, Dean. Or did you forget that I’m the one you came to for help blackmailing your way out of it?”

“It’s not like that-”

“So what, were you not able to get out of it? Or did he rope you in again to get you out of prison?”

“Why haven’t you come to me about this?” Bobby demanded. “I coulda helped you out.”

“I don’t _need_ help! I’m fine, guys, seriously. I’m not trapped in any deal or anything like that.”

“Is he threatenin’ you?” his voice grew more heated. “Because I don’t care how powerful this guy thinks he is-”

“Bobby, _stop!”_ He breathed out a long breath, shaking his head. “Crowley hasn’t done anything, so just leave him alone, okay?”

“Hasn’t done anything?” Sam asked incredulously. “Dean, you’ve told me about this guy, he-”

“He saved my life, Sam,” he said firmly, meeting his eyes. “I wouldn’t be standing here right now if it weren’t for him.”

“And so now you think you owe him?” Bobby asked.

“No, I-” He shook his head, refusing to look at any of them. “I just think I was wrong about him.”

“Dean, I can assure you that that is not the case,” Castiel said. “If Crowley did indeed save your life, then I am grateful, but I am also certain that he did it for his own selfish reasons.”

“You don’t know him as well as you think you do.”

The room went silent as soon as the words left Dean’s mouth, and he cursed himself silently. It was one thing to express that Crowley saving his life had left an impact on him, it was a whole other thing to claim that he knew him better than someone who had worked alongside him for the past two years. So much for diverting suspicion.

“I just mean, you only see the worst in him because that’s what you want to see,” he amended. “I did too, at first.”

Castiel took a step forward. “I don’t know if you are saying these things because you believe them to be true, or if it is because Crowley has threatened you. Either way, you once encouraged me in my mission to clean up the prison that my brother has corrupted. You said that I may only be able to do small things to make life better for the prisoners, but if you have evidence against Crowley, I can do more than that. I can-”

Dean raised a hand to stop him, his face twisted in anger and mild disbelief. “There are far worse people in that prison than Crowley,” he said as calmly as he could manage. “And he actually keeps them in line somewhat. So you might want to rethink who you’re going after.”

“Don’t you see that you are demonstrating exactly why Crowley is potentially the most dangerous guard at the prison?”

“Dangerous? Sure! But-”

“Dean, would you listen to yourself?” Sam implored. “You’re defending a guy that blackmailed you. And don’t try to tell me he didn’t,” he added quickly.

“I didn’t say Crowley was perfect. Hell, I didn’t even say he was good! But he’s not the evil incarnate that Cas wants to make him out to be.”

“But how can you-?”

“How can _you_ stand there questioning me when just last night you said that you understood what I was dealing with?” he demanded harshly. “That it didn’t matter, that you’d cut me some slack. It’s like one step forward, two steps back with you!”

“Funny,” Sam said softly. “I was thinking the same thing about you. I thought you were finally opening up to me last night – that even if you weren’t ready to tell me everything, there wouldn’t be any more lies. And now this.”

“And now… what exactly? Now you don’t trust me? Now you refuse to believe anything I say? Now you’d rather think that I’m stuck in some kind of awful deal than believe I’ve decided that someone isn’t _quite_ as deplorable of a human-being as I thought? You know what?” He shook his head, laughing bitterly. “I’m done. Whatever I say, you’ll only listen to what you want to hear.” Apparently, it didn’t matter whether he was lying or telling the truth anymore, his own family would label everything he said as a lie.

“Dean, you can’t just walk away from this,” Bobby said sternly.

“Watch me.” His eyes rested on his brother for a moment as he turned around, and he was angry enough that it almost didn’t hurt to see the grief in his eyes. It was Sam’s own fault, he told himself. This certainly wasn’t how he had wanted this day to go. “Sorry, Sammy, but I’m gonna have to skip out on the movie. But hey, maybe you can go with your new best friend.”

If Sam did reply, Dean did an excellent job of blocking it out. In a matter of seconds, he was back in the safety of the Impala, more than ready to put as much distance as possible between himself and his family.


	15. Truth

Dean took back every thought he had ever had about dogs being stupid. Juliet was probably smarter than a lot of people, and certainly more intuitive.

Dean had come home, gone straight to the fridge to grab as many beers as he could carry, and then collapsed on the couch to watch some meaningless TV show that he wasn’t even really processing. He had only gotten down his first gulp of beer when Juliet started her whining.

“What?” Dean demanded, his tone crasser than he had been with her in some time. “You have to go outside?”

She proceeded to jump up onto the couch beside him and nuzzle his hand, trying her best to squeeze her head beneath it. Dean eventually relented and began petting her with his free hand; immediately, she laid down, resting her chin on his leg and looking up at him with puppy dog eyes that an overly-grown pit bull should not be able to pull off.

“You’re never this cuddly with me,” he muttered, shaking his head slightly.

Juliet let out another low whine and twisted slightly so that she was pressed even closer.

He sighed. “I’m fine.”

If dogs had a look of disbelief, that was the look that Juliet was giving him at that moment.

“Hey, I knew that being with Crowley would mean sacrifice. I didn’t know that sacrifice would be my entire relationship with my family and a good friend, but what can I do?”

She whined again.

“And now I’m complaining about my life to a freakin’ dog,” Dean muttered before downing the rest of the beer.

By the time Crowley got home from work, there were five empty beer bottles on the table, and a sixth half-empty bottle in Dean’s hand.

“Dean?” Crowley called from the entryway, an irritated note in his voice.

Juliet’s ears perked up slightly, but she didn’t go running to greet him as she usually did.

“In here,” Dean answered, his voice slightly subdued.

“Is there something you want to tell-” Crowley stopped as he turned into the living room and saw the state Dean was in. “What happened?” he asked softly.

He shrugged without turning around to look at him.

“Alright.” He walked around the front of the couch, scrutinizing Dean with a concerned expression. “Does it have anything to do with the reason your brother paid me a little visit today?”

 _“What?”_ Dean demanded, slamming his beer down on the table and earning a protesting bark as he dislodged Juliet from his lap and shot to his feet. “Why the hell did he do that?”

“To threaten me,” he said with a dismissive wave of his hand. “And tell me that I’d better stay away from you.”

He grit his teeth as he shook his head. “Did anyone see?” If any of the other guards at that prison had seen a Winchester talking to Crowley, Dean knew how bad it would be. And if _Lucifer_ had seen…

“I don’t think so. And frankly, I’m more worried about you right now. What happened today? I thought things were going well.”

“Yeah, I thought so too,” he sighed, sinking back down to the couch and allowing Juliet to reclaim her spot on his lap. “But Cas came to see him today. Told him his suspicions about us.”

“And now Sam believes it, too,” Crowley guessed.

“And Bobby. He’s hellbent against you, now.”

“Bollucks,” he cursed. “Dean, if they manage to stack up evidence against me-”

“They won’t,” he assured quickly. “I-I’ll figure something out.”

“Not that I doubt your ability to wriggle your way out of sticky situations, but what exactly did you have in mind?”

He wracked his brain. What could he do to convince the family that he had just walked away from not to persecute the man that they surely blamed for it? “I don’t know yet. But I’ll think of something. I promise.”

“Dean,” Crowley sighed. “There’s only one solution I can think of.”

Dean perked up slightly. “Yeah? What is it?”

He hesitated. “Whatever case they may build against me will hinge, at least partially, on what Castiel has told them. If I discredit him…”

“What? Crowley, part of our deal was that you would protect Cas!” Even though he was furious with the guy right now, he couldn’t forget how the guard had stood by him, had put his job at risk for him. And honestly, the idiot really did think he was doing the right thing.

Crowley’s eyebrows shot up. “Our deal? I thought we were past that.”

He frowned slightly. “What do you mean?”

“I mean, I thought it was more than a bloody _deal_ keeping you here!” His eyes darted down as he huffed out a breath of air. “I _thought,_ with the way things were…”

“It _is_ more than a deal keeping me here,” Dean jumped to assure him. “I just… thought we were still – you know – under contract. I mean, you’re still sending Sammy money, aren’t you?”

“Of course. But that’s for you, not because we’re ‘under contract.’”

“Oh.” He wasn’t really sure what to say to that.

“But if that’s the way you see it-”

“It’s not. I mean, I did think our deal was still in effect, or whatever, but I told you I love you, and I mean that. I’m here, no matter what.” Even if Crowley’s business wasn’t Dean’s ideal way of earning a living, he wasn’t going to back out now. Whenever he started something, he saw it through to the end. And being in love with Crowley might also have something to do with it. “Damn, that’s the cheesiest thing I’ve ever said. I hope you realize that.”

Crowley chuckled, the corners of his lips twisting up briefly, before he became more serious again. “Then I’m asking you, as the man I love, if you could make peace with me discrediting Castiel to stop him from doing far worse to me?”

“I…” He made a fair point, but Dean just couldn’t stand by and watch as Castiel lost everything. “Let me see if there’s another way first, okay? He’s really done a lot for me, I owe him one.”

“Yes, and you started working for me to protect him, didn’t you?” he pointed out. “I’d say you’ve paid him back.”

“Yeah, I guess,” he muttered. It had never been about paying him back, though. Castiel was his friend, even if that friendship had been strained as of late. “I’d rather not just leave it at that, though. Let me call Sam… see if I can work this out.”

“No offense, but your brother doesn’t exactly seem to be the most understanding.”

“Well, if it doesn’t work, we can go with your plan,” he said as he once again removed Juliet from his lap and got to his feet. He didn’t leave room for any further debate as he pulled his phone out of his pocket and began dialing Sam’s number on his way out of the room. It had never been so crucial that a conversation between him and his brother should go well. And it had never been less likely that it would.

Sam answered on the first ring. “Dean?”

“What are you doing, Sam?” he demanded bluntly.

“What – what am _I_ doing? What are you even talking about?”

“I know you went to the prison today. You can’t do that! I told you that most of the people there hate our family, it’s not safe for you there.”

“It was safe enough when I was visiting you,” he argued.

“That’s because they already had me. They didn’t care as much about you. But if Lucifer had seen you-”

“How did you even know I was there, Dean?” he interrupted without any real question in his voice. He already knew, and there was no lie that Dean could tell him that would make him think any different.

“It doesn’t matter. Even ignoring the danger you put yourself in going there, you had no right. Look, what do I need to do to convince you that I’m not in some kind of deal with Crowley?”

“Oh I don’t know, how about you tell me the truth?”

“I _have_ been telling you the truth,” he insisted. “Prison-”

“Changed you. Yeah, I got that. And I can see distancing yourself because of it, but downright avoiding us? And everything Castiel said… well, it would explain a lot about how you got out… how I suddenly have money and a full ride to Stanford.”

Damn. Dean had kind of been counting on Sam _not_ piecing all of that together. “Cas was the one sending you guys money,” he said, a note of desperation in his voice.

“I figured that out,” Sam said calmly. “But the money I’ve been getting since you got out of jail… it’s not just a little to help out each week, it’s-”

“It’s from me,” he said quickly.

That caused him to pause. “What?”

“I’ve been sending you the money.”

“How?” he demanded. “Mechanics don’t make that much, Dean. I don’t care if Gunner Lawless is a customer of yours.”

Dean was out of options. There was only one thing that could explain how he had access to so much money – or at least, only one thing that Sam might actually believe. “Fine,” he sighed. “If you want the truth, I need you to swear to me that this stays quiet. Please.”

Sam thought that over for a moment. “I’ll consider it,” he said finally. Dean knew that was as good as he was going to get.

He took a deep breath. “I’m dating Crowley. It’s… pretty serious, actually. We couldn’t say anything because he could lose his job over it.” He braced himself for the fireworks.

“You’re… you can’t be serious! You can’t expect me to believe that.”

He scoffed. “Hey, you wanted the truth. You want me to put him on the phone, so you can hear it from him? He’s in the next room.”

“Dean, Cas says-”

“Cas doesn’t know him,” he cut him off sharply. “Not really. Look, I’ll admit Crowley’s not the most upstanding person in the world, but he’s not the devil incarnate that Cas makes him out to be. He… has another side to him. It surprised me too when I started falling for him.”

It took Sam a couple minutes to process that. “I don’t see what this has to do with the money I’ve been getting,” he said finally.

“Crowley’s parents were super rich,” he lied easily. It was much more convincing than most of the lies he had been telling lately, after all. “They left him everything. And he’s good at investing.”

“And yet he works as a prison guard?” he asked skeptically.

“He likes working for a living,” Dean shrugged. “He’s weird like that.”

“But-”

“But I hated him? But he blackmailed me? But he’s a total asshole? All true statements, Sammy. Doesn’t change that I love him.”

He could easily picture the shocked and mildly disgusted expression on his brother’s face as he shook his head. “How?” was all he managed to get out.

Dean got what he was really asking. “Well, you know how I had you help me find evidence to blackmail him out of blackmailing me?”

“Yeah…”

“I figured he’d be pissed, but he was impressed.” He coughed. _“Really_ impressed, if you get what I’m saying.”

“Uh, yeah, I get it,” he said quickly.

“So yeah, things kind of just escalated from there. He got me out of prison, and now we have to be paranoid-level careful about everything because if Lucifer finds out, he’ll have his head.”

“I see…. You said you love him?” he asked tentatively.

“Yeah,” he sighed. “Yeah, I really do.”

“And… does he feel the same?”

“Sure does.”

Sam sighed. “What am I supposed to tell Cas?” he asked after a minute.

“That you’re not gonna pursue any action against Crowley,” he said simply.

“He’ll want an explanation.”

“So make something up.”

He could practically feel Sam’s glare through the phone. “I don’t want to lie to him, Dean. He’s really helped us out.”

“So, tell him you believe me. That’s not a lie, is it?”

“No, I guess not,” he sighed.

“See, this is why I didn’t want to tell you. I knew it would put you in a tough situation, and really, the less people who know, the better.”

“Yeah, but I’m your brother. I want to know these things. And I was really worried about you, Dean.”

“Well, I’m fine.”

“Still… I’d like to meet Crowley properly. You know, see for myself that he’s not as bad as Cas says.”

Oh, that was bound to go over wonderfully. Still, he knew it would be worse to come up with some kind of excuse. Sam would go right back to doubting everything he said. “Alright, sure. Sometime before you go back to school-”

“How about tomorrow?”

“Tomorrow?” Dean blinked. “Tomorrow’s Thanksgiving.”

“Yeah, so? You said things are pretty serious between you too, right? So, why don’t you bring him to dinner?”

He blanched. Crowley at Thanksgiving dinner… just when he had thought he couldn’t dread the occasion any more. “Yeah, uh, okay. I can do that.”

“Great. We’ll see you both tomorrow, then.”

“Yeah… see you tomorrow,” he said reluctantly, feeling slightly sick. Oh, he just couldn’t wait to see Crowley’s reaction to _this._


	16. Thanksgiving

When Dean walked back into the living room, he was unsurprised to see that Juliet was now curled up on the couch with Crowley, who shifted to look at him as he entered the room.

“So?” he asked, his expression doubtful.

“You want the good news or the bad news?” Dean asked as he walked around the couch to sit down on the other side of Juliet.

He arched an eyebrow curiously. “I generally prefer to hear good news, unless it’s only bad for someone else.”

“Okay, well, they’re not going to try to get you arrested or fired or anything.”

“Well, that’s something,” Crowley said, clearly surprised. “So, what’s the bad news?” he asked with a slight frown.

“You’re coming to Thanksgiving dinner tomorrow.”

He blinked. “What?”

“I had to tell him we’re dating – it was the only explanation he’d buy.”

“Alright, but… I’m not exactly the kind of guy you take home to your family for Thanksgiving.”

“You don’t think I know that?” Dean demanded, shaking his head. “Sam invited you, and if I said no, he’d get suspicious again.”

“Because I’m sure he’s not at all suspicious of my intentions dating you.”

“Well, it’s better than it was.” He sighed. “Look, I don’t want to do it either, but we don’t have a choice.”

“Sure, we do. I could get called into work-”

“He’d be able to find out from Cas that you didn’t.”

“I could be spending the holiday with my family-”

“I told him your parents died and that’s how we have so much money.”

“I could get sick-”

“He’d _know_ that’s an excuse.”

“I could-”

“Stop it! Okay?” he snapped. “This is important to me. No, I don’t want to do this, but if we can make it work out, then maybe I can actually start talking to my family again.”

Crowley sighed. “Fine. What time is dinner?”

* * *

 

“I haven’t decided if you’re more cute or annoying when you’re nervous,” Crowley muttered as they approached Bobby’s front door.

Dean threw him a glare. “Shut up.” He took a deep breath and then knocked on the door. While he was sure that Sam must have spoken to Bobby about what was going on, and that Bobby would have called to say something if he had a problem, he still felt awkward just walking into the house with Crowley. Besides, there was no longer a point to pretending that everything was normal. They were far past that.

Sam opened the door, his expression an odd mix of emotions. Dean could definitely pick out apprehension and discomfort, but that was just scratching the surface. “Dean. Hey.” His eyes flickered uneasily to Crowley.

“Hey, Sam. You’ve met Crowley.” He nodded towards Crowley without taking his eyes off of Sam, unsure of how he was going to act towards him. How bad were things between him and his brother if he expected _Crowley_ to be the more civil one here?

“Pleasure to see you again,” Crowley said politely, extending his free hand for a handshake.

Sam’s arms were crossed over his chest, and he looked down at Crowley’s hand as though he’d rather not have to touch it. A moment passed, the only sound a car in the distance, and then Dean cleared his throat pointedly, and Sam sighed and reached out to shake his hand. “I gotta admit,” he said coolly. “I didn’t think you’d actually come.”

“Well, Dean can be very persuasive. He gave a rousing speech about the importance of family, and I couldn’t say no.”

“Now that sounds more like the Dean I know,” Bobby said as he walked up behind Sam. “So. You must be Crowley.”

“In the flesh,” he said as he released Sam’s hand. “And you must be Bobby. I’ve heard a lot about you.”

“Likewise. Though I can’t say I’ve heard anything good.”

“Of course not,” Crowley said dismissively. “I go to great lengths to ensure that nothing good about me gets spread around. Ruins my image.”

“Hmph. Well, come on in.” He took a step back, and Sam followed suit. “I’m giving you a chance for Dean’s sake, but I _will_ kick you out if I decide you’re no longer welcome here.”

“What a lovely, warm welcome,” he murmured as he walked inside.

Bobby pulled Dean into a hug almost as soon as he stepped inside. “I’m sorry about yesterday,” he muttered. “I’m just worried about you.”

“I know, Bobby,” Dean sighed as he stepped back. “But really, I-” He looked over at Crowley and smiled slightly. “I’m good.” He turned back to his uncle, his expression apologetic. “Sam told you why I couldn’t tell you guys?”

“He told me your excuse.”

“Right…” He rubbed the back of his neck uncomfortably. “So, when’s dinner?” he asked after an awkward minute.

“About ten minutes.”

“Where would you like this pie?” Crowley asked, offering out the tin he was holding.

Bobby jerked his head toward the kitchen. “C’mon, I’ll show you.”

Dean made to follow after them, but Sam stopped him with a hand on his arm. “I need to talk to you about something.”

He closed his eyes as he gave a sigh, pretty sure of what was coming. “If this is about Crowley-” he started as he turned to face him.

“It’s not. Well, not how you’re thinking, anyway.” He let out a deep breath. “Look, after I got off the phone with you yesterday, I-”

He was interrupted by a knock at the door.

Dean turned around with a frown. “Are we expecting someone else?”

“Dean,” Sam began, but he was already opening the door, revealing Castiel standing on the front porch.

“Cas,” Dean said in surprise, a note of suspicion coloring his voice. He shifted slightly so that he was blocking the doorway. “What – what are you doing here?”

Castiel frowned slightly. “Sam invited me.”

“Sam…?” He rounded on his brother with a glare. “What the _hell?”_ Was this whole Thanksgiving dinner just to trick him into _another_ intervention? This time with Crowley there to suffer along with him?

“That’s what I was trying to tell you, Dean,” Sam sighed, stepping up beside him and shooting Castiel an apologetic look. “After I got off the phone with you yesterday, I called Cas. It came up that he didn’t have anyone to spend Thanksgiving with, so… I invited him here.” He gave a small shrug. “That’s the only reason. Promise.”

Well, that was a small relief. Not enough to make him relax, though. “Okay. But what about… _you know…?”_

“That fact that you and Crowley are dating?” Castiel asked.

Dean looked between the two of them in disbelief.

“I couldn’t lie to him, Dean,” Sam said apologetically.

“I don’t care!” he shouted. “What part of what I told you made it sound like there was another _choice?”_

“There’s always another choice! Cas is our friend, or have you forgotten that because _Crowley_ doesn’t like him?”

“This has nothing to do with whether or not he’s a friend! It’s about Crowley not ending up fired, or worse, all because you couldn’t-”

“Dean,” Castiel interrupted calmly. “Before your brother told me anything, he made me swear that I would keep it to myself. And I intend to keep my promise. As much as I believe that this is in the running for the worst idea you have ever had, I will not report your relationship.”

Before Dean could fully process his words, Crowley emerged from the kitchen, and he turned to face him, his doing so giving him a clear view of who was standing in the doorway. “Dean, is everything – oh.” His gaze went cold as his eyes rested on Castiel. “So, this is how it’s going to be, is it?”

“As I was just explaining to Dean, I have no intention of reporting your relationship,” he said evenly, though his expression had gone just as cold as the other man’s. “Sam made me promise, and besides, I value Dean’s friendship.” He took a step forward, his eyes narrowing. “But if I find reason to believe that there is something more going on…”

“Don’t try to threaten me, angel,” Crowley said coolly. “It doesn’t work for you.”

“Are you idjits goin’ to stand out here bickering for the rest of the day, or are we going to celebrate Thanksgiving together?” Bobby demanded as he appeared in the kitchen doorway.

Dean sighed as he turned back to Castiel. “You’re really not going to get Crowley fired?”

“Not over this, at least,” Castiel said solemnly.

He supposed that would have to do. “Fine. Then… I’m glad you’re here.” He offered him a small smile before turning and meeting Crowley’s gaze.

The other man sighed. “Well, I’m not going to say I’m glad too, if that’s what you want.”

“I take no offense.” Castiel gave a small shrug. “I cannot say that I am glad to see you, either.”

“Oh, Cassie – how sweet.”

Dean shot an exasperated glance at his brother, and he could tell from the look on his face that he was only just now realizing how big of a mistake inviting Castiel might have been. This was going to be one hell of a Thanksgiving.

* * *

 

“So, how _did_ you two end up together?” Castiel asked as he helped himself to more mashed potatoes.

“I don’t see how that’s any of _you’re_ business,” Crowley said coldly.

“Well, I’d like to know, too,” Sam spoke up, meeting Crowley’s eyes with a challenging gaze.

“Of course you do,” he sighed.

“I already told you,” Dean said around a mouthful of stuffing. Sam and Crowley both shot him eerily similar looks of distaste.

“All you told me was that you started sleeping together in prison. That doesn’t explain how you got here.”

Castiel frowned. “You slept together _in_ prison? How did you manage that?”

“Why? Looking for some pointers?” Crowley teased. “Who’s caught your eye?”

He actually blushed slightly at that. “No one in prison, I assure you.”

Sam cleared his throat, and Dean recognized the expression of somebody who was trying very hard not to look at someone in particular. He smirked slightly as his brother spoke. “Would you stop avoiding every question with a sarcastic comment?”

Crowley opened his mouth – probably to prove that he would _not_ do such a thing – but Dean hastened to cut him off. “We kept hooking up even after I got out of prison. Actually, I kinda… moved in with him as soon as you went off to college.”

“Cause that was better than stayin’ here, I suppose?” Bobby demanded gruffly.

“It wasn’t like that,” he sighed. “I was telling the truth when I said I just didn’t feel right staying – I had changed too much. Crowley got it, though. He was easier to be around.”

“But it was just sex at that point?” Sam clarified.

“Sort of…. But then I went out with Gunner, and he got all jealous-”

“Excuse me?” Crowley interrupted. “You went out with Gunner to _make_ me jealous.”

Dean rolled his eyes. “And it worked, didn’t it?” he countered with a smirk.

“If I recall, _you’re_ the one who made a scene over me finding my own company for the night.”

“I didn’t _make a scene-”_

“You gave me a black eye!”

“Okay, guys, I think we get it,” Sam sighed.

“I gave you a black eye because you were throwing a hissy fit over me moving out,” Dean snapped, ignoring his brother.

“And _why_ were you moving out again?” Crowley demanded.

Bobby leaned over to mutter to Sam, “Hate to break it to you, but I think they’re telling the truth.”

Dean’s gaze snapped to the two of them. “Telling the truth about what?”

Sam’s gaze flickered to Bobby, who simply looked at him pointedly, then he sighed. “That you guys are dating,” he said reluctantly.

He scoffed, nodding his head. “Of course. Because you didn’t _actually_ want Crowley to come today to get to know him better – it was all a test.” He had already suspected as much, but it was one thing to suspect, and another to know.

“Dean-”

“Is that why Cas is really here, too?” he accused. “To see if this is all a sham and then to turn Crowley in?”

“Dean, I assure you,” Castiel said solemnly. “As much as I would love to turn Crowley in, that is not why I am here today. Sam and I were merely discussing Thanksgiving plans, and when I mentioned that I had no one to spend the holiday with-”

“Yeah, but that’s bullshit, isn’t it? Your dad’s still around, right? And don’t you have, like, five brothers?”

“Four,” he corrected. “And my father isn’t exactly… _around._ After he retired, and Lucifer _somehow_ managed to get the job of warden, even though it had been promised to Michael, he began traveling. It was probably so that he wouldn’t have to see how our family was torn apart, even though he was the only one who stood a chance at putting it back together. I barely remember a time when he was around.” He sighed. “And as for my brothers, Lucifer is obviously not even worthy of the title, and I have not spoken to Michael or Raphael since I took the job at the prison. They believe it is heresy to work for Lucifer, even if the point is to improve the prison.”

Dean didn’t let Castiel’s story sink in, didn’t let himself feel bad for the guy. “Okay, but what about Gabriel? You guys get along great.”

He hesitated for just a moment. “He is at Lucifer’s.”

“What?” Crowley demanded, while Dean blinked in surprise. “I know Gabriel is still stuck in the good ol’ days where his family is concerned, but having Thanksgiving dinner with _Lucifer-”_

“I did not say that he was having dinner _with_ Lucifer, merely that he is at his house.”

“Oh, thanks for clearing that up,” Dean rolled his eyes.

“Lucifer is at work. Gabriel is having dinner with our nephew, Jack.”

“Because that’s _so_ much better,” Crowley muttered.

Castiel’s eyes narrowed. “Jack cannot be judged for the person his father is. Speaking of which, Gabriel told me how you treated him on Halloween.”

“What can I say? I hate kids,” he said unabashedly. “And that goes double for any child of Lucifer’s.”

“Oh, isn’t that nice,” Sam muttered, his gaze moving to Dean. “Guess there won’t be kids in your future, then?”

“Really, Sam?” Dean demanded irritably. “We’ve been dating for less than three months. If it were anyone else, you wouldn’t be questioning us about kids.”

“Maybe I would if they came out and said that they hated kids,” he argued.

“Yeah, right,” he scoffed. “And you know, I’ve never even said I wanted kids.”

Crowley looked at him sideways, his expression mildly concerned. “Do you?”

“No! I mean, I’ve never really thought about it,” he admitted. “But I don’t think this is a conversation we need to have right now.”

“I guess I just always pictured you being a father,” Sam said softly. “You were so good with me growing up…”

Dean looked at his brother and his expression softened slightly. “Yeah, but you were a pain in the ass. Why would I want to go through that again?”

The corners of Sam’s lips twitched. It wasn’t much, but it was something.

“If you idjits are finished arguing, I’m about to serve up the pie,” Bobby said as he got up from the table.

Dean flushed slightly. “Sorry, Bobby.”

He shook his head. “Don’t be. You two needed to get that out.” His gaze moved to Sam and he cleared his throat pointedly before turning away to get the pie.

Sam sighed. “I am sorry for not trusting you, Dean. It’s just… there have been so many lies lately-”

“I know.” Dean nodded. “And I’m sorry, too. But I told you why I had to.” Why he still had to.

Sam nodded. “Yeah. Yeah, I get it.”

Dean found himself smiling. Maybe things would get better, after all.


	17. Ultimatum

The rest of Thanksgiving dinner had gone well, for the most part. Sure, things were a bit awkward, and it was certainly no secret that Sam was not overly fond of Crowley, but they didn’t fight the entire time, so that was something.

“You gonna have to face Cas today?” Dean asked the next morning, eating a bowl of cereal as he watched Crowley cleaning his dishes before he would have to leave for work.

He shook his head. “I’m pretty sure he’s off today. Sure wish I was, too,” he added with a sigh.

He frowned. “Something wrong?”

“Lucifer’s been… off lately.”

His eyebrows furrowed slightly. “Off how?”

“It’s hard to explain,” Crowley said as he finished up and leaned against the counter, facing Dean. “I feel like I’m being scrutinized, though, and I don’t like it.”

Dean straightened up, his cereal forgotten. “You think his kid said something?”

“I don’t know…. If he did, I’m not sure what exactly Lucifer’s playing at. Which makes me even more nervous.”

“You could ask Gab-”

“And have him jump down my throat again for accusing his precious nephew? Besides, it’s not like he’d know anything.” He sighed. “Sometimes I wonder why I still work there.”

“It’s good for business,” Dean pointed out, even though he had to admit that it would be nice if Crowley only had to work one job.

“But not essential. Sure, it was at the beginning, but we don’t need to lean on the work we get from the prison, anymore.”

“Yeah, but a part of you likes it. Despite Lucifer.”

He shrugged as he pushed away from the counter. “I’d like it more if I were in charge.”

Dean chuckled. “You like everything more when you’re in charge.”

Crowley grinned as he walked over to give him a kiss. “I’ll see you tonight.”

Once Crowley was gone, Dean headed up to the study to make a dent in the duties that he and Crowley had fallen behind on by taking Thanksgiving off. He had just gotten off the phone with Marsha – a delightful conversation, as always – when his phone began ringing, ‘Sam’ popping up on the screen.

“Heya, Sammy,” Dean answered the phone. He reached down to open the mini fridge he had convinced Crowley to add to the room. He could use a break, anyway.

“Hey,” Sam said with a note of hesitancy in his voice. “Um, I’ve been talking to Cas…”

“Yeah?” he smirked slightly as he grabbed a beer and then straightened up. “You two dating yet?”

“I – what? No.” He cleared his throat. “Look, I wanted to figure out why he suspected Crowley so much in the first place. And before you say anything, I’m not accusing you of lying again. I just don’t think you know-”

“You just don’t think I know my own boyfriend as well as Cas does, is that it?” Dean interrupted coolly. He took a breath to calm himself. Of course this mess wasn’t over yet. “Look, I know Cas thinks he’s this horrible person, but if he had done half the things that Cas has accused him of, he wouldn’t still be a prison guard.”

“Oh right, just like that guy, Alastair, you told me about?” Sam countered. “Or Azazel? He was still a guard after he murdered our mom! So no, Cas might not have enough evidence to prove that Crowley has struck deals with _multiple_ inmates, and possibly even some dangerous people outside the prison, but the suspicion comes from somewhere. And I do know for a fact that he has blackmailed at least one person.”

“Sam-”

“And your friend, Benny? Turns out, Crowley’s who got him out on parole. And I went to that restaurant he works at, and his ‘good connection’? Also Crowley. He made a deal with him, I’d bet money on it.”

“No, he didn’t,” Dean sighed. “It’s not what you think.”

“No? Dean, he’s lied to you! I did some digging into his family, and there’s no record of his father. And his mother – who I’m pretty sure is still alive, by the way – never had any kind of fortune. However he came by his money, it wasn’t honestly.”

Dean stared down at his untouched beer. He didn’t see how he was going to be able to get them out of this one. Even Crowley’s solution of discrediting Castiel was no longer an option – Sam had even more information than he did, at this point. He shook his head slightly. Just when things were getting better…. “You been researching him since we left yesterday?” he asked tonelessly.

“Pretty much. Look, Dean, I know you don’t want to hear this-”

“Haven’t you learned your lesson about prying into the lives of dangerous people?” he sighed.

Sam paused. “I just told you that your boyfriend is lying to you, and you’re-”

“He’s not lying to me,” Dean said resignedly. He knew there was no lie he could tell Sam that would fix this. He could only try to get him not to do anything with what he now knew.

“Dean, I’m telling you – I know the blackmailing and making deals are all conjecture, but the stuff about his family-”

“Is true. Yeah, I know. I mean, I don’t know the details – he doesn’t like talking about his family – but I know enough.”

“But you… you told me his parents died and left him his money…”

“Because I couldn’t tell you the truth.”

Sam took a deep breath. “It’s all true. You really did make a deal with Crowley. You two were really just putting on a show last night.”

“No, we weren’t-” But Sam wasn’t listening.

“Why didn’t you just tell us?” He demanded. “Whatever Crowley’s threated, he won’t get away with. We have enough to use against him, we can-”

“Sam, _stop!”_ He shook his head. “You want to know what Crowley does? He runs an organization that blackmails and strikes deals with all the most powerful people around – almost all of this town is in the palm of his hand.” He took a deep breath. “And I’m his right-hand man.”

“Only because you’re forced to be! But if we-”

“No, Sam,” he said evenly. “I’m not forced to be anything.”

Sam was silent. “What do you mean?” he eventually asked cautiously.

“I mean, I’m working for Crowley willingly.”

“What? No, you…” he trailed off, his voice full of disbelief. “Crowley’s a criminal. Why would you work for him?”

“Because I love him,” he answered easily. “I wasn’t lying about that part, Sam.”

“But… how? I don’t… I don’t get it.”

Dean leaned back in his chair, bringing his beer up to his lips for a drink. “You want it from the beginning?”

“Will that help me understand?”

“Maybe.” He shrugged. “My first day in prison, Crowley tried to bribe me with protection from the other guards. I refused, but he kept trying. Then, after everything that happened with Azazel, he finally had a way to blackmail me. I worked for him in exchange for him keeping quiet that I had escaped.”

“Worked for him how?”

“I gathered information from other prisoners that he could use. We got close. And then I blackmailed him, and I already told you what happened after that.”

“But you kept working for him?” The confusion was palpable in Sam’s voice.

“No. But later he told me he could get me out of prison. I told him I wasn’t interested, until he said that I could ask for pretty much anything I wanted.”

“So, you got me money and a full ride to Stanford,” he guessed.

“Yeah,” Dean admitted with a sigh. “And I got Benny out on parole. And then… well, I told you the rest last night. But Benny never made a deal – Crowley got him that job as a friend.”

Sam was silent for a few seconds as he processed everything. “So… you never got a job as a mechanic?” he clarified.

“No.”

He sighed, and somehow the feeling of betrayal was audible in that small sound. “Everything has been a lie,” he said softly.

“I couldn’t exactly tell you that I was a criminal,” Dean said rationally, still trying to keep his emotions removed from the conversation. “I knew what you would say.”

“That this isn’t you? Because it’s not, Dean. My brother would never co-lead some blackmail ring, if he had a choice about it.”

“You sure about that? Because I’m pretty sure I’m doing just that.”

“But you can’t actually _like_ what you’re doing,” he argued.

“I’m good at it.”

“That’s not the same thing,” Sam sighed exasperatedly. “Tell me, if it weren’t for Crowley, would you be doing this?”

He sighed. “No. But that doesn’t matter because it _is_ for Crowley. This is his life, and I’m not leaving him alone in it.”

“He’s a _criminal._ How am I just supposed to stand by while-?”

“Because if you take him down, you’ll be taking me down, too,” Dean said evenly, desperately hoping that it would be enough to deter him from doing anything rash. And it had to be, didn’t it? “And I know you won’t do that, Sammy.”

“Actually, there are plenty of ways to go after just him,” he corrected.

“And you would do that?” he demanded, a note of disbelief in his voice. He got that Sam was trying to be the good guy here, but didn’t the fact that he loved Crowley at least mean _something_ to him?

Sam hesitated. “I haven’t decided yet.”

“Well, _don’t,”_ he said desperately. “Sam, I am happy where I am, with what I’m doing – the only downside is that I’ve hated lying to you about it.”

“That’s the _only_ downside?” he demanded skeptically. “I somehow doubt that.”

Dean sighed. “What do you want me to say? No, it’s not the kind of life I thought I’d be living. But it works. Sometimes you have to make compromises for the people you love.”

“Yeah, like what kind of cereal to buy, you shouldn’t have to compromise your values!”

“My values were already pretty screwed up,” he said with a shrug.

“Not this bad. Dean, if he really loved you-”

 _“Don’t,”_ he cut him off harshly. He knew where he was going with that, and it wasn’t a thought he needed in his head. “Don’t say that if he loved me, he wouldn’t be doing this, wouldn’t be dragging me along with him, because you don’t know Crowley like I do. This is his _life,_ Sam. I would never ask him to give it up for me.”

Sam was silent on the other end of the line. “I think I should go,” he said a minute later. “I have some things I need to think about.”

“Yeah, I think you do,” Dean sighed defeatedly before hanging up the phone. This was just great. Not only was his relationship with his brother completely destroyed, now everything else in his life was wrecked right along with it.

He tried to get back to work, but he couldn’t. He just stared down at the list of names and their current assignments, but he couldn’t concentrate enough to make sense of it all. What did it matter, anyway? Crowley could be arrested any day now.

He began to pace the house, and Juliet worriedly followed behind him, until Crowley got home. He frowned as soon as he saw the look on Dean’s face. “What’s wrong?”

“Sam knows,” he muttered without quite looking at him.

He was silent for a second as the weight of those two words sank in. “How?”

“The kid’s good at research. Found out your parents aren’t who I said they were, and that combined with everything Cas said…”

Crowley’s expression was blank, and Dean knew he was calculating their options. “Do you know what he’s going to do?”

“No. I don’t think he knows, yet.”

“Good,” he said, surprising Dean. “Then we can still sway him.”

Crowley wasted no time. He didn’t even bother to change out of his uniform before he ushered Dean to the car, and then they were on their way to Bobby’s.

This time, Dean didn’t bother to knock. He just walked right in, then turned into he drawing room, where he saw Sam sitting, talking to… Castiel. Dammit.

He froze in the doorway, Crowley right beside him, but the sound of the front door had already given away their entrance. Sam looked up, his eyes widening slightly as he saw them both standing there, and Castiel followed his gaze, his expression as hard to read as usual.

“What’s going on here?” Dean asked cautiously, though he already had a pretty good idea.

“Dean, I… I’m sorry,” Sam sighed as they both got to their feet. “I had to tell Cas.”

“Dammit, Sam!” He glared around the room, finding it difficult to look at his brother. “You didn’t have to do anything!”

“For my own peace of mind, I did,” he snapped.

Dean shook his head and looked over at Crowley hopelessly. He was glaring at Castiel through narrowed eyes. “So, all your suspicions about me have been confirmed. Congratulations. You still don’t have any real evidence, though.”

“You think we can’t find some?” Sam challenged.

“Him?” he jerked his head toward Castiel with a scoff. “No. You? Well, I know better than to underestimate your family.”

“Guys, come on,” Dean said imploringly. “Cas, you’re my friend – you said just last night that that means something to you. Would you cut Crowley some slack? For me?”

Castiel exchanged a brief look with Sam, who nodded. “You mean, will I allow Crowley to continue running criminal operations in a prison that I am trying to cleanse?” he asked solemnly as he turned back to Dean. “I think you know that I can’t do that.”

“But-”

“But because you are my friend, I hope that we can resolve this without having to involve anyone else.”

He blinked in mild surprise. “What do you mean?”

He eyes moved back to Crowley, turning slightly colder as they did so. “I am going to give you a choice-”

“Let me guess,” Crowley interrupted silkily. “Quit my job at the prison, or give up my side business?”

“Yes. If you refuse to do either, I won’t have a choice but to pursue some course of action against you.”

“And I’ll help him,” Sam added. “We won’t stop until we bring you down.”

“I’m quivering in fear, really,” Crowley muttered, but Dean could see the worry creasing his forehead and the anger burning in his eyes.

“Sam, why?” Dean tried desperately. “Why can’t you just leave this alone?”

“Because you deserve better,” he said matter-of-factly. “And Dean, it’s not like we’re getting him arrested. It’s a fair choice. Talk it over together.”

Understanding lit Dean’s face at Sam’s pointed look. So, _that_ was why. He expected Dean to suggest that Crowley choose the prison, to admit that he hated being a criminal, anyway – either Crowley would listen to him, and Dean would find himself dating an honest man, or he wouldn’t, and Dean would see that he didn’t really care what he wanted, that he should never have been with him in the first place. It was a decent plan. The only problem was, this was Crowley’s decision, and Dean wasn’t about to sway him one way or the other.

“I’ll give you a week to decide,” Castiel said. “I believe that is generous.”

“You know, we could always bring up how you lied about killing Azazel.” Dean turned to Castiel, his face expressionless. “How you covered up my escape from prison.”

He appeared surprised by Dean’s threat, but the look on his face was nothing compared to Sam’s shocked expression. Still, Castiel’s voice was calm as he replied, “And I could say that Crowley was involved in that, too.”

“Are you sure?” he asked, taking a step forward. “Because it was _my_ escape that was covered up, and I think I’d know if he was involved. Which in the story I tell, he won’t be.”

“Dean,” Crowley spoke softly from behind him. “You’re not going back to prison for my sake.” He looked up at Castiel. “I’ll get back to you with my decision.”

Castiel nodded. “Thank you, Crowley.”


	18. Revelations

Dean and Crowley didn’t talk much on the drive home. Or for the rest of the night, really. Crowley just muttered something about needing to think, but what was there to think about? They both knew what his choice would be. He would never give up the empire that he had worked so hard to build, especially not for a job he had been thinking about quitting just that morning.

So, maybe it wasn’t the he needed to think. Maybe he was just angry with him for getting him into this position. Dean couldn’t exactly blame him. This was all his fault. Crowley would never have been given this ultimatum, if it weren’t for him.

Even with all of Crowley’s complaints about the prison, Dean know that a large part of him loved working there, and he had been working towards getting Lucifer’s job for years now. And now because of him, he’d never get it. He wondered if he’d ever be able to forgive him for that.

Crowley didn’t say much the next morning, either – just that he was scheduled to work a ten hour shift, and there was no telling if he’d get off on time, so Dean might want to go ahead and eat without him. So, Dean was a little surprised when Crowley walked into the living room just a couple hours after he had left. But he supposed that could only mean one thing – he had quit his job. Without even talking to Dean about it. Even though he couldn’t exactly blame him for that, it still hurt.

“Lucifer told me to go home early,” Crowley declared as he walked over and took a seat on an armchair.

Dean blinked and looked at him in incomprehension as the words clashed against his assumption. “What?” he asked blankly.

“He said I looked stressed, that I could use some time off.” He shook his head as he leaned back in the chair. “I told you he was acting strange.”

“Uh… yeah,” he muttered. “No kidding.”

He sighed. “But I have bigger things to worry about, so I’m not going to dwell on it.” His eyes flickered to Dean for a moment, then slid away, his expression far away. “I’ve always been able to get myself out of these situations before; I’ve been thinking of nothing else since we left yesterday. But I don’t think there’s a way out this time.”

“Come on, I’ve seen what you’re capable of.” He had assumed that they were stuck with this ultimatum, but Crowley was right, he’d gotten himself out of worse situations before, so surely…

“Perhaps no way out is an overstatement. There’s nothing that I am willing to do. Every potential solution ends with you getting hurt, one way or another.”

“That can’t be-”

“Step one – I have to discredit Castiel. I can either tell the truth about Azazel, which would get you in trouble for breaking out of prison, and get you scrutinized for another murder, _or_ I could easily dig up something else.”

“So, why not do that?”

Crowley looked at him like he was an idiot. “Because he’s one of your best friends.”

“Yeah, and I threatened him myself yesterday.”

“But you would never have gone through with it.”

“You don’t know that,” Dean argued.

“Yes,” he said confidently. “I do. You’re far too soft-hearted to go after those you care about. Just like you never would have carried out your threat to blackmail me.”

He blinked in surprise. “I might have!” he protested.

Crowley rolled his eyes. “No, you wouldn’t have. I was fairly sure of it then, and even more sure now.”

He frowned slightly in confusion. “So… why did you cave?”

He shrugged. “I wanted to see how things would play out. I knew I could get you back easily enough.”

He shook his head. “Wow. And here I thought I had successfully blackmailed you.”

“You did. And if you were just a little more heartless, I would have actually been worried.”

Dean sighed. “Well, it’s not like it matters, anyway. Look, don’t worry about me, if you have a way to get out of this mess-”

“Dean,” Crowley said gently. “Castiel isn’t the real problem here, and you know it.”

He was silent for a moment as he looked away from Crowley, staring out the window without seeing anything. “Yeah, I know,” he sighed.

“And as much as I would love to shut Samantha up, I would never do that to you.”

He gave a humorless laugh. “Well, apparently, you’re the only one who actually cares about not hurting the people I care about.”

He sighed. “Dean…”

Before he could come up with what to say, though, Dean’s phone began to ring. The both looked down at the name, ‘Sam’, flashing on the screen until it morphed into ‘5 missed calls’.

Crowley looked up at him, one eyebrow raised slightly. “Ignoring your brother?”

“I have nothing to say to him,” Dean said, glaring at the TV in front of him.

“Well, that’s fine… so long as you never intend to talk to him again.”

He blinked at him in surprise. “What?”

“Ignore him all you want, so long as you intend to stick to it. Otherwise, what’s the point? If you’re going to talk to him again at some point, why drag out the misery now?”

Dean’s eyes narrowed. “You sound like a freakin’ fortune cookie.”

“Please, I’m far smarter than any fortune cookie.” He nodded at his phone before rising to his feet. “You should call him. Meanwhile, I’m going to take Juliet for a walk. Maybe manage to clear my head.”

Dean stared sullenly at his phone as Crowley left the room, not wanting to admit that he made a good point. As difficult as it was to imagine having a civil conversation with his brother right now, it was even harder (and more painful) to imagine never speaking to him again. He sighed as he reluctantly picked up his phone.

“Dean,” Sam answered in surprise after the first ring. “I didn’t think you’d call me back.”

“I wasn’t going to,” Dead said gruffly. “But Crowley convinced me.”

There was a pause. “Crowley…”

“Yeah, Sam, _Crowley_ convinced me. Even after what you pulled.”

“Somehow I don’t think he did it for my benefit.”

“No, but he seems to think that talking to you will make me less miserable, so… here we are.”

Sam sighed. “Look, Dean, I know you’re pissed at me, and I get it – I’m sorry. But… I stand by what I did.”

“And I stand by that it was a dick move,” he said matter-of-factly.

“Dean-” He paused, taking a deep breath. “I know you love him, but that doesn’t mean you should have to have this life.”

“I don’t have to-” he immediately refuted, but Sam cut him off.

“But you feel like you do,” he said reasonably. “You don’t even want to tell him that you don’t like living like this. And don’t try to tell me you do!”

Dean sighed. “It’s not like I’m unhappy, Sam.”

“But you will be. Or you’ll lose yourself. One of the two.”

He didn’t say anything to that. Sam just didn’t understand. Yeah, it had sucked getting someone arrested that he had promised to protect; yeah, he often felt a little guilty after a job well done. But life wasn’t perfect. So no, this life wasn’t ideal, but he’d made his peace with it.

“I just wanted to give you the opportunity to tell him,” Sam continued when it became clear that Dean wasn’t going to say anything.

“Well, I’m not going to,” he said resolutely. He had already made that decision, whether Crowley asked for his opinion or not.

“Because you don’t care?” he challenged. “Or because you’re afraid he won’t listen to you?”

“Because I know what he’s going to choose! And I don’t want to make him any more conflicted than he already is.”

Sam was silent for a few seconds. “Has he even asked you what you think?” he asked quietly.

Dean hesitated, knowing how Sam would take the answer. “No,” he muttered. “But he doesn’t have to,” he added quickly.

“He should! This decision impacts you, so if he really cares about you-”

“Stop saying ‘if’, Sam. Crowley doesn’t work like most people, but I know how he feels about me.”

“Are you sure about that?”

“Yes,” he said firmly, then he sighed. “Look, Sam, I’m pissed at you, and that’s not changing anytime soon. If you’re not going to change your mind, then I think it’s best we not talk until this all settles down. Otherwise, we’re just gonna fight.”

“Guess Crowley was wrong about this making you less miserable, huh?” he muttered.

Dean frowned slightly as he thought about that. “Actually, I don’t think he was. Stewing in rage wasn’t helping anything, but… I need space right now, Sammy. At least until Crowley makes his decision. Then we can see where that leaves us.”

“Yeah, alright…” Sam muttered with a sigh. “Bye, Dean.”

“Yeah. Bye.” He hung up the phone and threw it back down onto the table before leaning back against the couch, feeling at least a little lighter.

A few minutes later, Crowley reentered the room. He studied his face for a moment before saying, “You called him, didn’t you?”

“Yeah,” he muttered. “He stands by what he did.”

“I didn’t expect anything less.” He shrugged as he sat down on the couch beside him. “But you feel better, don’t you?”

“A bit,” he hedged. “I’d feel even better if you didn’t have to do this, though.”

“Me too,” he sighed.

Dean looked at him out of the corner of his eyes. “You know, when you came home early, I figured you’d already quit.”

Crowley looked at him in disbelief. “I wouldn’t do that without talking to you about it. You should know that.”

He shrugged. “You don’t have to. This isn’t my decision to make.”

“Perhaps. But I’d like for you to have a say, all the same.”

 _Take that, Sammy._ He smiled just slightly, but shook his head. “No, Crowley. I know how important this enterprise is to you. I’m not going to sway you, one way or the other.” He placed his hand on his leg, squeezing lightly. “Thanks for caring enough to ask, though.”

Crowley was studying his face with a frown as he spoke. “Of course,” he muttered, his eyes flickering away.

“I’m gonna go get a beer.” He patted his leg as he rose to his feet. “You want anything?”

“No, thanks,” he murmured, appearing to be deep in thought.

Dean nodded and left the room, scratching Juliet behind the ear on his way out.

*

The days ticked by, and Crowley still hadn’t made his decision. He still went to work at the prison, and he still came home and carried out his work in the study. If Dean didn’t know better, he would think he was in denial.

“Crowley,” Dean said softly Wednesday evening, leaning against the doorway of the study. “You know you only have two days, right?”

“I know,” Crowley sighed, laying the file he was holding down on his desk and staring at it. “I’m just… going through things. Hoping it’ll help make a decision.”

He was about to point out that they both knew what he was going to choose, but he stopped himself. Giving up work at the prison was clearly even harder for Crowley than Dean realized. If he needed to go through their files to remind himself how much he loved the business he had built, then he should do just that. “I’ll leave you to it, then,” he muttered. He started to turn to leave, but Crowley’s voice stopped him.

“You know, I would still like you to weigh in.”

Dean sighed as he turned back, seeing that Crowley was looking up at him now. “And I’m still not going to.”

His eyes narrowed slightly. “Why not? I know what you want, Dean, you don’t hide it that well. So, why not just say it?”

He stiffened slightly. “If you know what I want, then you know why.”

“And yet I’m still asking.” He met his gaze in that challenging way of his that made it clear that he wasn’t backing down.

“What do you want me to say, Crowley?” he demanded, his temper flaring. Couldn’t Crowley see that he was doing this for him? Sacrificing what _he_ wanted for him? “That I never wanted this in the first place? That if I keep living like this, I don’t know if I’ll ever be able to salvage my relationship with my brother? It doesn’t matter! I know what you’re going to choose! And that’s fine, really. I love you, and your choice isn’t going to change that. So, just… choose for yourself, okay?” He spun on his heel and nearly bolted from the room before Crowley could say anything.

That was far more than he had wanted to say, and it left him feeling slightly sick. First, he had gone and put Crowley in this situation in the first place – even though Crowley had assured him multiple times this week that he didn’t blame him, Dean was still furious with himself – and now he had gone and made the choice even more difficult for him. Of course, he didn’t think for a second that what he had said would change his decision – now Crowley would just end up feeling guilty whenever he did admit that he was leaving the prison. And now that Crowley definitely knew the truth, the choice would sting, even though Dean knew it was coming.

After staring aimlessly at the TV for a few hours, absorbed by his own guilt, Dean eventually made his way back upstairs, pausing for just a second when he heard a voice coming from the study, a voice that wasn’t Crowley’s. But of course, he was probably listening to some of their recordings of various important conversations. It wasn’t until he was turning into the room that he realized what recording he was listening to.

“She knew who I was… what I had done. She loved me unconditionally. She forgave me. She only asked for one thing. So, I turned my back on Abaddon, on the business that we had built together, and I started a life with her.”

Dean swallowed thickly as he remembered Cain saying those words to him, remembered how wistful he had felt, and how he had quickly shoved the feeling away because Crowley would never love him like that.

Crowley’s eyes were unreadable as he looked up from the computer, his gaze resting on Dean. He quickly tried to school his features, wiping any sadness from his expression.

“We were happy, for a short while,” Cain continued, before Crowley reached out and paused the recording.

“Dean…”

The doorbell rang.

Dean frowned, glancing behind him, towards the stairs. “Were we expecting anyone?”

Crowley didn’t say anything as he got up and moved to look out the window. His entire body stiffened. “Stay here,” he muttered as he spun around and stalked from the room.

Dean’s frown deepened as he passed him. “Who is it?”

“Just… stay here, Dean,” he repeated desperately, without stopping.

He stared after him as he descended the stairs, his eyebrows furrowed in confusion. _Like hell,_ he decided, and hurried after him.

By the time he caught up to Crowley, he was opening the front door. Standing on the front porch was a tall, blonde woman, beautiful in the dangerous kind of way, and beside her was a timid-looking young boy who couldn’t be more than twelve or thirteen.

“What the _hell_ are you doing here?” Crowley seethed, oblivious to Dean standing a few feet behind him.

“Crowley,” the woman said coolly. “You remember your son?”


	19. Decisions

Dean stared at the scene before him in utter disbelief. She had just… but Crowley didn’t… but this boy was…? He shook his head as though that would help to dispel his confusion, then he focused his gaze on Crowley, who didn’t even glance at the boy that was apparently his son.

“What are you doing here, Lilith?” he demanded again through gritted teeth.

The woman – Lilith – rolled her eyes. “You haven’t changed one bit, have you, Crowley? You stand there like you’re on top of the world; it’s almost as though you forgot that I’m the one that put you there.”

“You always did want to give yourself all the credit,” Crowley said, his voice ice cold. “But I never needed you.”

Lilith’s laugh was like bells. “No? When I found you, you were pathetic – a sad drunk who couldn’t get over how his mommy never loved him. Then I remade you. Of course, you were a natural – I never would have bothered, otherwise – but you would not be where you are now, if I hadn’t set you on that course.”

“I wouldn’t be so sure.” His voice was low and deadly. “Now, if you came here just to reminisce, I’m afraid I’m not interested. Get off my property before I force you off – dead or alive, I really don’t care.”

Dean looked down at the boy, who looked decidedly uneasy. He reached out to tug on Lilith’s sleeve, but she slapped his hand away.

“You think _I’m_ afraid of _you?”_ she demanded with another ringing laugh.

Crowley took a step forward. “Alright. You want to reminisce, let’s reminisce. Let’s see… I believe the last I heard of _you_ was that Lucifer had stirred up some trouble with the wrong people, and you took the fall for him. Fell right off the face of the earth, it seemed like. You know he hasn’t mentioned you since, right? You sacrificed yourself for him, and he didn’t even care.”

Dean quickly took a step to the side to better insure that Lilith couldn’t see him. If she had ties to Lucifer…

“Lucifer is dead to me,” she spat, all humor gone from her voice.

“That so?” Crowley, on the other hand, sounded vaguely amused. “So, you’re done worshipping the ground he walks on, then?”

She scoffed. “You always were so jealous of him.”

“Oh no, I just thought you were embarrassing, the way you would do anything for him, the way you were practically begging him to use you. You even tricked me into having a bloody kid, just so you’d have children the same age!” He motioned towards the boy, acknowledging his presence for the first time since he had opened the door. “You figured he’d never tire of you, then. Oh, how wrong you were.”

The silence that stretched between them seemed palpable with the anger that coursed through it. At last Lilith spoke, her voice cold. “Now that you mention Gavin, that’s actually why I’m here.”

Crowley stepped back and grabbed hold of the door, his knuckles going white from gripping it so hard. “Goodbye, Lilith.” He started to shut the door, but she slammed her hand against it, holding it open.

“You want me to say that you were right?” she demanded angrily. “Fine – you were right. The only reason I wanted a child was for Lucifer’s benefit. Then I spent _ten years_ in slavery because of him, with nothing but this boy.” Disgust twisted her voice. “But now I’m free, and I am not about to be tied down by this little brat.”

He actually laughed at that. “You can’t be serious. I’m not the one that wanted him in the first place.”

“I don’t care. I’m done with him. So, you can either take him, or I’ll just leave him on the street.”

“No. _No!”_ Crowley’s voice had taken on an angry and horrified edge. “You cannot show up here on my doorstep and expect me to-”

Dean had had enough. He didn’t know who Lilith hated more right now between Crowley and Lucifer, but he couldn’t just stand there and watch this kid be scarred for life, so all he could do was hope that it was Lucifer, and that this wouldn’t come back to bit them in the ass. He strode forward, yanking the door out of Crowley’s hand so that he could stand in front of Gavin, bending down slightly to get closer to his level. He smiled gently. “Hey – Gavin, right?”

The boy shot an anxious glance at his mother, then nodded.

“My,” Lilith murmured. “I see your choice of pet has improved. Is this who I think it is?”

Crowley ignored her. “I told you to wait upstairs,” he said tightly.

“And I didn’t listen,” Dean said with a shrug. He glanced briefly at his anxious expression, finding it hard to feel bad at the moment, then turned back to Gavin. “You look hungry. How ‘bout I get you something to eat?”

The kid looked between Lilith and Crowley nervously, apparently too scared to answer. Dean didn’t know much about this Lilith, but he already hated her.

“It’s Dean Winchester, right?” Lilith asked, turning to him. “I saw you on the news. I immediately recognized the name, of course – Azazel had been absolutely obsessed with your family.”

“And look where that got him,” Dean snapped, glaring at her.

She shrugged. “Can’t say I’m surprised. He was always a fanatic. Lucifer would mention something he wanted, and Azazel would blow it out of proportion – it was bound to get him killed one of these days.”

“And you were so much better?” Crowley sneered.

Dean’s gaze was fixed on Lilith as he straightened up. “What do you mean, something Lucifer wanted?” he asked slowly.

Lilith’s eyes sparkled. “You thought Azazel acted of his own initiative? How cute.”

“Crowley, what’s she talking about?” he demanded without looking away from her.

“Nothing,” he said firmly. “She’s playing you.”

Dean shook his head, knowing he was probably right. He clearly knew Lilith pretty well, after all. “Why don’t you just let me take your son to get some food?” He kept his voice as even as possible. “I think he’s heard enough of you two arguing.”

Lilith’s eyes flickered back to Crowley. “He’s good-hearted for a killer, isn’t he?”

“He’s good-hearted for anyone,” Crowley corrected coolly.

Her gaze swept over Dean curiously before she looked down at her son. “Well, go with him, Gavin,” she snapped.

The boy quickly stepped to Dean’s side, and he placed a gentle hand on his back and guided him away.

“Does Lucifer know the company you keep?” he heard Lilith ask behind him.

“You’re not the only one who gave up being a good and faithful servant.”

Dean lead Gavin into the kitchen and motioned for him to sit down.

“What would you like to eat?” he asked kindly.

Gavin shrugged.

He supposed he shouldn’t be surprised that he wasn’t speaking. Gavin didn’t know him, and he couldn’t imagine that Lilith had ever encouraged him to speak much, anyway. He decided to just make him a sandwich, and then he served it to him with some water and a slice of blueberry pie. Out in the entry way, he could hear raised voices, but he couldn’t make out what they were saying.

“How old are you, Gavin?” Dean asked as he took a seat across from him.

Gavin took his time chewing his bite of sandwich before he answered, “Thirteen.”

“Oh, that’s a good age. I got my first girlfriend when I was thirteen.”

He just looked at him as he ate his sandwich.

Dean cleared his throat uncomfortably. “I’m Dean, by the way. I’m, uh… dating your father.” Now _that_ was weird to say. Crowley was a _father_.

There were another few seconds of silence. “You didn’t know about me, did you?”

Damn, the kid was intuitive. He sighed. “No, I didn’t,” he admitted reluctantly. “But the thing about Crowley is that he doesn’t like to talk about his past, he-”

“He hates me.” The statement was matter-of-fact, with just a touch of sadness in it.

“No, he doesn’t-”

“How would you know? He hasn’t told you he doesn’t.” He looked down at his plate. “Lilith said he abandoned us when I was two.”

“Well, I think that was more because of her-”

“And then he let me get thrown into slavery with her,” he went on, a touch of anger in his voice now.

Dean leaned back in his chair. Yeah, this kid was going to have some issues. “You shouldn’t have had to go through that,” was all he could think of to say.

There was the sound of footsteps and then Crowley entered the room, holding a backpack and looking thoroughly unhappy. “Lilith’s gone. She left this, though – I assume it’s yours?” He held the bag out to Gavin without quite looking at him, and the boy took it and hugged it to himself.

Dean sighed as he rose to his feet. “I think we need to talk,” he muttered.

Crowley gave a curt nod, avoiding eye-contact.

He turned back to Gavin. “Will you be alright for a bit? Do you need anything else?”

Gavin appeared surprised at being asked. “I’m fine.”

He nodded, and he began to walk away, Crowley following behind him. The other man paused at the door, turning back to his son. “Just stay there and… don’t get into anything.”

Dean shot a glare over his shoulder, but continued walking. Once they reached the drawing room, he closed the doors behind them and then rounded on Crowley. “What the hell, Crowley?” he demanded.

He sighed. “I should’ve told you,” he muttered, his eyes fixed on a spot in the corner of the room.

“Well, yeah. But how about we start with why you’re further traumatizing an already traumatized kid?”

He did look at him at that, blinking in surprise. “What did I do?”

“Oh, I don’t know? How about make it clear that you want nothing to do with him? How do you think he felt listening to his parents argue over who would be stuck with him?”

Crowley looked down. “This is why I don’t do kids.”

“And you don’t have to – we can find him another family to take him in. But after everything he’s been through, don’t you think he could use some kindness?”

“I’m not ‘kind’, Dean, you know that.”

Dean rolled his eyes. “Then, how ‘bout you go for not being a total ass? We’re not gonna find him a good home overnight – you’re going to have to learn to live with him for at least a little while. And I’ve got news for you, he ain’t your biggest fan.”

“Can’t say I’m surprised,” he said with a shrug. “I’m sure Lilith’s told him plenty of horrible things about me.”

He shook his head. “That’s only a small part of it. You knew that Lilith got into trouble, that something bad would happen to him, and you never did anything about it.”

“He was her son, not mine, as far as I was concerned. I never wanted him.”

“Yeah, and that’s not gonna mess the kid up,” he shot at him.

Crowley shrugged. “He was always going to be messed up – he has the two worst parents in the world.”

“And you never wanted to do _anything_ to prevent that?”

“Yes,” he said matter-of-factly. “I never wanted to have a kid in the first place.”

“Well, now you do,” Dean said firmly. “You can’t change that. Just… try to make life at least a little better for him while we’re looking for a home.”

He still appeared skeptical of his ability to do anything decent for the kid, but nevertheless said, “Fine. So long as he’s not too much of a brat.”

He sighed irritably. “He’s thirteen – he’s going to be a brat. But there are ways to help that without being all…” He motioned towards him with his hand.

“Without being me?” he asked with an arched eyebrow. “Got it.”

“You know what I meant.” He shook his head. “Look, you’re not alone in this. You know that, right?”

From the surprised look on Crowley’s face, Dean guessed that he hadn’t realized that. “I figured, given that I kept all of this from you…”

“I mean, I’m not happy about that, but I’m not going to leave you over it. You want to tell me why you never felt inclined to share that you had a son?”

He sighed, then walked over and sank down onto a chair, staring at the blank TV screen, his gaze far away. “I was at my absolute lowest when I met Lilith,” he began, as Dean wandered over to sit on the couch. “Just the way she carried herself, she exuded success – power. It was enticing.

“When I first approached her, she laughed in my face. But I was persistent, and I suppose she saw something in that because she took me in as her little project. She’d been friends with Lucifer since grade school, so she was easily able to get me a job at the prison. But she did more than that. She showed me how to make people do whatever I wanted, and like she said, I was a natural.”

“Wait, so… does Lucifer know what you do?” Dean asked, his eyebrows furrowed in confusion.

“A bit,” he hedged. “He knows I strike deals with prisoners – encourages it, even, so long as it suits his interests. He even knows a little of what I get up to outside the prison. I give him cuts occasionally to stay on his good side, but he has no idea how little of a portion I’m actually giving him. He has no idea how much of this town is under my control.” He sighed. “Anyway, Lilith and I never actually cared about each other, but neither of us were looking for that, so we worked, as a couple. But then Lucifer started talking about how he wanted a son, how he wanted to prove that he could be a better dad than his father was. Honestly, I think Lilith wanted to be the mother, but he preferred a nobody that he could easily get out of the picture, so she decided on the next best thing – that we would have a child of the same age to be Lucifer Jr.’s best friend, or maybe even lover.

“I didn’t find out that she had stopped taking her birth control until she announced that she was pregnant. I was furious, of course, but I stuck it out. We started fighting more and more after that. I couldn’t stand how blindly loyal she was to Lucifer, and of course, I had to hide that I was hating him more and more every day. Growley was the last straw.”

Dean drew in a deep breath. “She’s who let him out.”

He nodded. “She was mad at me. It never occurred to her that she had crossed a line, and then I was gone. Back then she was more than happy to keep the kid, since she still had plans of Gavin and Jack growing up together. But then she helped Lucifer out of a jam and he threw her under the bus.” He shrugged indifferently. “He explained it all to me afterwards – wanted to make sure I understood that he had had no choice, that Lilith had outlived her potential. Really, I knew he was just trying to gage whether or not I’d try to avenge my ex, but of all the things he should have been worrying about where I was concerned, that was not one of them.

“He never told me exactly what kind of mess Lilith had landed herself in. For all I knew, she and the kid were both dead.”

“And you didn’t care,” Dean accused.

“I had no attachment to a son I didn’t know and had never wanted in the first place,” he said simply. “Honestly, I never cared about anyone but myself until I met you. And I’m not trying to be sappy here, it’s just the truth.”

“Alright,” he sighed. “So, you never told me because…?”

“Because it wasn’t important. I’ve always preferred my past to stay in the past, so why bring up a son I never expected to see again?”

“Well, it’s a pretty crappy reason, but I guess I see your point.” He rose to his feet. “C’mon, we should probably get back to Gavin – you can meet your son properly, and we can find him a room.” He didn’t like the idea of Gavin sitting in the middle of that big kitchen all alone – not after everything he had been through. “Once we work out this mess we’re currently in the middle of, we can start looking for someone to adopt him,” he added.

“Actually,” Crowley said as he stood. “We’re not in the middle of another mess. I was going to call Castiel tonight to tell him my decision.”

Dean blinked in surprise, feeling a tightening in his chest. “Oh…. Well, good. That’s good,” he muttered, turning away slightly. It was inevitable, he reminded himself. There had never been any other way this was going to end.

“I’ll need your help informing the others we’re disbanding,” he continued nonchalantly.  

It took him a moment to process that, but his words still didn’t add up. “…What?”

Crowley caught and held his gaze. “I’m done with our organization. I’m keeping my job at the prison.”

“But… it’s your life.”

“And it’s made me miserable.” He shook his head slightly. “You know, I’ve been focused for so long on staying on top. Never realized I hated it. All those whining employees, the endless complaints, the paperwork! I mean, who wants that?”

Dean found himself smiling slightly. “You’re sure? I mean, you’re not just doing it for me?”

He shrugged. “Of course it’s for you, but I also think it’s for the best. And no trying to change my mind on this,” he added quickly when Dean started to open his mouth. “You made it very clear that you wanted no part in this decision. This is my choice.”

He chuckled slightly as he took a step toward him. “Fine, you win. And thank you.”

Crowley just smiled and pulled him into a kiss.


	20. New Life

When Dean and Crowley returned to the kitchen, Gavin immediately got to his feet, his expression unreadable. Looking between the two of them, Dean wasn’t sure he ever would have guessed that they were related. They really didn’t look all that similar, aside from that look on Gavin’s face – it was the same look Crowley got whenever he was trying not to show that he was hurt.

“I guess I’ll be going now?” he asked, looking intensely at a spot on the floor.

Crowley froze. “What?”

“You’re throwing me out, aren’t you?” He looked up at Crowley’s face as though he already knew exactly what he’d see there. It was a dangerous mindset, Dean knew, because it meant that no matter what he saw in his father’s eyes, he’d translate it to mean that he didn’t want him there. “It’s not like you actually want me. You’ve made that clear my entire life.”

He hesitated, and Dean nudged him gently. He took the hint and took a deep breath as he stepped forward. “It’s not that I… don’t want you. I just wouldn’t be a good father. It was never about you.”

Dean smiled at him encouragingly. It wouldn’t mend the wounds that Crowley had inadvertently inflicted upon the boy, but it was definitely a step in the right direction.

Gavin nodded. “Of course. I’m sure slavery was a much better option.”

But apparently it was nowhere close to enough.

“I…” Crowley cleared his throat. “I didn’t know what you were going through.”

“You knew _something_ was going on.” His eyes flashed with anger. “So, maybe you thought I was just going to be killed? Or thrown in jail? Still better than you being my dad, right?”

His eyes flickered down, but when he looked back at Gavin, his gaze was steady. “Honestly? I never gave it much thought. Lilith got you both into trouble – we hadn’t spoken in almost a year – it was out of my hands.”

Gavin made a noise of disgust. “I used to think my father must not know about me, but when I asked Lilith, she told me you knew, you just didn’t care. I didn’t want to believe her, but I guess she was telling the truth.”

“Gavin-”

“Maybe you’re right. Maybe you being my dad really is worse than all that. So, go on – throw me out on the street. It will be better than where I came from, and that’s better than you, so…”

Crowley snorted, and Dean saw something in him snap. Before he could do anything to stop him, though; he was already speaking. “You know, I was going to try to help you, but if you’re going to be so _ungrateful-”_

“Of course. Sorry.” He glared up at him. “Thank you for abandoning me.”

“Gavin-” Dean started.

Gavin turned to look at him, some of the hostility fading from his eyes. “Bye, Dean. Thanks for the food.” He grabbed his backpack and pulled it on with a sudden whimper of pain.

Dean frowned, but Crowley spoke before he could. “You’re hurt.”

He turned his glare back on him. “Lilith got mad. What do you care?”

Crowley seemed torn. But after several seconds, he took a step forward. “Let me see.”

“Why?” Gavin took a step back. “So you can make it worse?”

“No. So I can make it _better.”_ He stared him down, and reluctantly, Gavin dropped his backpack and turned around, raising the hem of his shirt. There was a gash across his back, and it appear that his backpack scraping across it had opened the wound, causing fresh blood to mix with the dried blood that was already there.

Crowley sucked in a breath. “What did she do to you?” he demanded softly.

Gavin’s voice was more hesitant when he spoke now. “I questioned her, and she was holding a knife, so she…” He swallowed thickly. “I shouldn’t have, but I didn’t want her to bring me here.”

“No, _she_ shouldn’t have.” He looked over at Dean. “Dean, could you get me the first aid kit?”

“Course.” Dean nodded and nearly dashed from the room. He couldn’t get the image of Gavin’s blood-stained back from his mind. How could Lilith do that to a _kid?_ Her own son?

He grabbed the first aid kit and a wet washrag, and then hurried back to the kitchen. When he returned, Gavin had his shirt off and was sitting on a chair with Crowley standing behind him.

“You know, I had a pretty horrible mother, too,” Crowley was saying conversationally.

“Yeah? That why you are the way you are?” Gavin asked, half cold, half curious.

“Probably.”

There was a pause as Dean quietly walked forward and set the supplies down on the table, not wanting to interrupt them.

“Do you think it would have been better if she wasn’t around?” Gavin finally asked as Dean backed away.

He knew he should probably give them some privacy to talk, but there we also the chance that Crowley would need him as backup – and admittedly, he was curious; Crowley never talked about his family. His curiosity won out and he lingered a few feet away from them.

“She wasn’t, really,” Crowley admitted. “She left when I was eight.”

“So, do you wish she hadn’t, then? That you still had a mother, even if she wasn’t a good one?”

The pause was longer this time. Crowley began cleaning Gavin’s wound, his expression an unreadable mask that matched his son’s. “Yes,” he said quietly, almost a minute later.

“But you still thought I’d be better off without you as my father?” Gavin demanded, a trace of indignation in his tone.

“I said I wished she hadn’t left – not that I wasn’t better off without her.”

“So why-”

“For the same reason you wish Lilith hadn’t left,” he cut him off matter-of-factly. “The same reason a part of you is hoping you’ll be staying with me. Humans have a tendency to want the exact _opposite_ of what they need.”

Gavin appeared to think that over for a minute. “So, you really think I’d be better off on the street?” he asked evenly.

Crowley opened his mouth, but then appeared to reconsider his words and closed it again, looking over at Dean for help.

Dean gave him a small smile as he shrugged. “You seem to be doing an alright job to me.”

He sighed. “I suppose not,” he admitted. He finished wrapping his wound and took a step back. “But it’s your choice, Gavin. I won’t force you to stay.”

Gavin turned around and looked up at him thoughtfully. “Lilith told me that you blackmail people.”

He blinked in surprise – whether the surprise was due to the fact that Lilith had told Gavin about what he did or more because Gavin had brought it up, Dean wasn’t sure. “I have been known to do that, yes.”

“So… you can get people… important people… to do whatever you want?”

Crowley’s eyebrows furrowed slightly, and Dean knew they were both trying to figure out where Gavin was going with this. “I have before.”

“And if I was to accept you as my father, you could use that to get _me_ what I wanted? Or keep me out of trouble, no matter what I do?”

Dean had to hold back a laugh. He really was his father’s son.

Crowley’s gaze was incredulous, though the corners of his lips were curling up slightly. “You’re negotiating with me?” He chuckled. “That’s my boy.”

“So, is that a yes?” he asked hopefully.

He shook his head slightly. “I don’t do that anymore. But… I suppose if you were to get into trouble, I’d be able to pull some strings.”

For the first time, Gavin’s lips turned up into a small smile. “I won’t have to suffer anymore.”

“Not like you have.” He reached out, placing his hand on his shoulder. “I’ll make sure of it.”

Dean smiled as he walked forward. “So, Gavin. Does this mean we should find you a room?”

Gavin thought about it for another couple of seconds, and then he nodded. “Yes.” He turned back to Crowley. “Bad father or not, for the first time I feel like I can actually have something good.”

“Well, let’s hope you’re right,” Crowley murmured as he handed Gavin his shirt.

They found Gavin a room on the second floor, a few doors down from theirs, and after ensuring that he had everything he needed, they left him alone to get settled. Then they walked back down to the living room, where Crowley proceeded to collapse onto the couch. Dean smiled as he moved his legs aside to sit down on the end, maneuvering Crowley’s feet to rest on his lap.

“What a day,” Crowley sighed.

“I’ll say,” Dean agreed, allowing his head to rock back against the couch. “You did good with him, though.”

He raised his head slightly to look at him in disbelief. “You call that _good?”_

“Alright, you got off to a rocky start, but it all worked out. Calming him down, that was all you.”

“Still not sure I’m cut out for this,” he muttered.

“Then you should make sure the kid understands this is only temporary. Otherwise he’ll feel betrayed when you’re suddenly sending him off to some other family.”

Crowley didn’t say anything.

“Crowley?” Dean pressed after a minute.

He sighed. “Should I, though?”

He frowned. “Should you what?”

“Send him off to some other family. The boy’s been through a lot.”

“Yeah, and he could probably use some stability,” he admitted. “But he can find that stability elsewhere. Unless… you’d rather he stay here.”

“I don’t know what I’d rather, anymore.”

“So, tell me what you’re thinking,” Dean prompted.

“I’m thinking… I’ve been where he is. I want to give him the chance that I never had, do for him what my mother never did for me.”

He nodded. “So, do it,” he said simply.

“Like it’s that simple?” Crowley threw back at him, shaking his head slightly.

“We can at least give it a shot.”

“Do you really want to raise a temperamental teenager with a fucked-up past?” he challenged.

“Hey, I’ve been there,” he said with a shrug. “I’m not saying this is a dream of mine, or anything, but I’m not opposed.”

“So, what do you propose?” His voice was slightly mocking. “He can call me ‘father’, and you ‘dad’, or-”

“We’ll figure it out with time,” Dean cut him off, exasperated. “And you’re the one who brought this up. If you don’t want to-”

“I didn’t say I don’t want to, but do you remember what I said about how people tend to want what’s worst for them?”

“You don’t really believe that,” he argued. “At least not in everything, and not with this. I think Gavin could actually be good for you.”

“Oh? How so?” he asked skeptically.

“You’ll need somewhere to focus all that extra energy once you’re only working one job,” he said with a slightly teasing grin. “He’ll challenge you – in a good way, I think.”

Crowley sighed as he turned and straightened up into a sitting position. “So, I suppose it’s an honest life _and_ fatherhood that I’m choosing today.”

Dean chuckled faintly. “Guess so.”

He turned to look at him through narrowed eyes. “You are far too much of a good influence on me, Dean Winchester. I hope you realize that.”

“Hey, it’s my pleasure.”

He sighed as he pulled out his phone. “Speaking of an honest life, I suppose I’d better get this over with.”

Dean watched as he pulled up Castiel’s number and called it, putting the phone on speaker.

“Hello?” Castiel answered.

“Hey, Cassie,” Crowley said conversationally. “You want my decision?”

“Of course. I would not have answered your call otherwise. It is not as though I enjoy conversations with you.”

He rolled his eyes. “Well, you’re going to have to deal with them, because I’m staying on at the prison.”

“But your business…”

“That’s right, I’m quitting my life’s work all for you. Well, all for Dean, but still, you’re the one making me do it.”

“I _thought_ I was making you quit your job at the prison,” Castiel said, his frown audible in his voice.

“Ah, that’s the thing about blackmailing people. You have to be very clear on what you want. If you give people a choice, things might not work out the way you hope.”

“How do I know you’re really going to stop everything else you’ve been doing?” he demanded. “You’ve managed to keep it secret in the past, you could simply be attempting to do so again. I cannot trust you.”

“So, what about me?” Dean spoke up. “Can you trust me?”

“I thought I could,” he said sadly. “But the last time we spoke, you threatened me.”

“Well yeah, you were threatening Crowley – I didn’t have a choice. Just like you didn’t have a choice when you had a chance to clean up the prison some. But honestly…” He glanced at Crowley. “I don’t think I could’ve gone through with it. You’re still my friend, Cas. And as your friend, I promise you, Crowley’s telling the truth here.”

There was a pause on the other end of the line. “Alright. I suppose I will see you at work, then.”

“Yes, you will,” Crowley said smoothly before he hung up the phone and slid it back into his pocket. “It’s done.”

Dean wasn’t surprised when, an hour later, he got a call from Sam.

“Calling to admit you were wrong?” Dean asked when he picked up the phone.

“I was wrong about what he’d chose, but I wasn’t wrong that it was the best thing for you. Was I?” Sam challenged.

He sighed. “Too soon to tell.” Maybe someday he’d tell Sam that it felt like a weight had been lifted from his shoulders, that there wasn’t the painful twinge of guilt whenever he though of what his future might hold, but he couldn’t admit that just yet.

“So… you’re still mad, then?”

“Yeah, and I’m gonna be for a while. But… we’ll work through this.”

“Good.” There was a moment of uncomfortable silence. “So… everything good between you and Crowley?”

“Yeah, everything’s great,” Dean said as he flipped the burgers he was grilling. “We kind of have a son now,” he added nonchalantly.

Sam made a choking sound. “Wh-what?”

“Crowley’s long-lost son turned up at our front door today. Congratulations, you’re an uncle.”

“But…” He seemed to struggle to remember any words. “But doesn’t Crowley hate kids?”

“Yeah, but… this one’s his. And it shows.” He smiled fondly. “He’s decided to give fatherhood a shot.”

“Wow.”

“Yeah.”

They talked a little more as Dean finished up making dinner, mostly about Gavin and how Dean felt about the whole thing, and then Dean said goodbye so that he could go get Gavin for dinner.

“Hey, dinner’s ready,” he said as he pushed the door open.

Gavin had been laying on his bed, seemingly staring off into space. He sat up when Dean spoke. “Okay… Dean, can I ask you something?”

“Of course,” he said, stepping into the room.

“Why are you with my father?” he asked curiously. “You seem like very different people.”

“We are,” Dean said with a nod. “In some ways, at least. But sometimes I think we’re more alike than we realize. It’s… hard to explain, but I love him.”

“So… you’re not going to leave?” There was worry in Gavin’s voice, and Dean realized that he hadn’t really been all that curious about his and Crowley’s relationship, he’d just wanted to make sure that Dean wasn’t just some fling that was going to be leaving in a matter of weeks. Even though he had just met this kid, it meant a lot to know that he wanted him to stick around.

Damn, how much his life had changed in one day. Yesterday he’d been running a criminal organization and wasn’t sure he’d ever be able to talk to his family again. Now he was unemployed, things were on the mend with his family, and he was helping to raise a thirteen-year-old boy who it seemed did, in fact, want him as a dad.

He smiled as he looked Gavin in the eye and said as firmly as he could, “I’m not going anywhere.”

**Notes for the Chapter:**

> There are still two more parts to this series - To Hell and Back and Little Piece of Heaven - but I'm going to be taking a bit of a break so I can focus on some of the other works on my 'To Write' list. I have at least one multi-chapter fic that I'm really itching to write, and after that I'll probably continue this series. 
> 
> I hope you enjoyed! Your comments and kudos give me life!


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